James Kenner, 13 April 1885 - 30 June 1974rsbm.royalsocietypublishing.org/content/roybiogmem/21/389.full... · James Kenner, 13 April 1885 - 30 June 1974 Lord Todd, F. R ... matriculation

James Kenner, 13 April 1885 - 30 June 1974

Lord Todd, F. R. S.

1975, 389-405, published 1 November211975 Biogr. Mems Fell. R. Soc.

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JAMES KENNER

13 April 1885 — 30 June 1974

Elected F.R.S. 1925

By Lord T odd, F.R.S.

James Kenner was born on 13 April 1885 at Morpeth in Northumberland but his family came originally from Devon. His father, James Binmore Kenner, was born at Stoke Damarel in 1856, the son of a tailor’s seamster, but the family moved to London in his early boyhood. There they lived in humble circumstances in Soho Square and Kenner’s father, after only a primary school education, was sent out to work at an early age. However, he became a pupil teacher at St Martin’s Church School near Charing Cross and by his own effort and selfteaching matriculated at London University and then passed the Intermediate Arts Examination and was appointed an Assistant Master at Morpeth Grammar School in Northumberland about 1877. There he graduated B.A. London as an external student, a truly remarkable achievement for a self-taught man. In due course he became Second Master at Morpeth but in 1891 he gave up his post there to take over a small private boarding school at Brentwood, Essex, and developed it until he had about 100 boarding and day pupils; he retired in 1920 and died in 1940.

Young James received his school education at Brentwood and passed London matriculation in June 1897; thereafter he entered the East London Technical College (now Queen Mary College) intending to study mathematics. However, while at school he had attended classes in chemistry given by a former pupil of Meldola named Hughes, whom he described as an inspiring teacher. As a result he passed the Science and Arts Department Advanced Stage Examinations in chemistry, both theoretical and practical, and at East London he attracted the attention of Professor J. T. Hewitt who persuaded him to change to chemistry; in December 1904 he graduated B.Sc. with first class honours in chemistry having already demonstrated his precocity by publishing with J. T. Hewitt and H. Silk his first scientific paper (1) ‘On the bromination of phenols’ in 1904. Hewitt persuaded Kenner’s father to send his son to study further in Germany and at Easter 1905 the young chemist went to Heidelberg to work with Professor E. Knoevenagel. It was the custom in those days to require an entering Doktorant to undertake first a preparation from the literature, and Kenner was told to prepare benzenesulphinic acid from aniline by diazotization. He then confirmed

389



390the original observation of Friedel & Crafts (1878) that benzenesulphinic acid could be prepared from benzene, sulphur dioxide and aluminium chloride, but the yield was very poor. Following a suggestion of Knoevenagel (based no doubt on Gattermann’s aldehyde synthesis) Kenner modified the reaction by carrying it out in the presence of anhydrous hydrogen chloride and obtained a yield of 80%. Extension of this work to other examples formed the subject- matter of his Ph.D. thesis ‘Uber Friedel-Crafts’sche Synthesen mit Hilfe von schwefliger Saure in Gegenwart von Salzsaure’ (2) which in turn formed the basis of a paper with Knoevenagel (3). Having completed his Ph.D. work at Christmas 1906 he returned to England the following Easter to take up a teaching post at the small Hipperholme Grammar School near Halifax; while there he gave W. Sucksmith (later to become Professor of Physics at Sheffield and a Fellow of the Royal Society) his first lessons in science. School teaching was not to his liking, however, and when in 1909 his former teacher J. T. Hewitt gave him the opportunity to enter academic life he seized it and was appointed Assistant Lecturer with Professor W. P. Wynne at Sheffield. It was never likely that Kenner would take easily to the repressive and rather feudalistic atmosphere of the Sheffield Chemistry Department, and indeed he did not, but in autobiographical notes which he left with the Society he acknowledged that, on the whole, Wynne left him free to develop his own research ideas. In accordance with the view, based on his Heidelberg experience, that it was desirable always to have a variety of researches going on simultaneously in a laboratory, he quickly got to work along three different lines, namely the study of aromatic nitrocompounds, the preparation of j^zVo-compounds, and the formation of compounds containing a seven-membered ring from 2:2'-ditolyl.

Research on nitro-compounds led to the submission of a thesis ‘The influence of nitro-groups on the reactivity of substituents in the benzene nucleus’ for which he was awarded the London D.Sc. in 1914. Slightly abbreviated, the contents of the thesis were also published in the Journal of the Chemical Society (16). Interrupted—as indeed was all his research—by World War I, the work on nitro-compounds was restarted on his return to Sheffield and led to the publication of a further nine papers. It is noteworthy, too, that this interest in nitrocompounds was, in the writer’s opinion, indirectly responsible for the initiation of most of the important work done by Kenner up to the time of his retirement— including that on diphenyl derivatives and on nitroso-compounds.

During these pre-1914 years J. F. Thorpe was Sorby Research Fellow in the Sheffield Chemistry Department, his main research interest at that time being the study of glutaconic acid. There was evidently a good deal of contact between him and Kenner; this was reflected in Kenner’s paper on the condensation of ethyl glutaconate which led to a proposal that they should collaborate in the synthesis of s/wVo-compounds from cyc/ohexane-1:1 -diacetic acid. For some obscure reason this collaboration was forbidden by Wynne, an autocratic action which exacerbated the already strained relations between him and Kenner, who then turned his attention to the Bouveault-Blanc reduction of ethyl hydrindene-2:2-dicarboxylate; the hoped for di-alcohol was obtained in very

Biographical Memoirs



James Kenner 391

small yield only and attempts to improve it and to use the product as a starting point for preparing ^/ro-compounds were terminated by the outbreak of war. The route originally envisaged from ryc/ohexane derivatives was, of course, developed in due course by Thorpe at Imperial College.

The third group of researches in the pre-1914 period was perhaps the most interesting, since it represented the start of what was to be Kenner’s most lasting achievement. Shortly after arriving in Sheffield he was set the task of revising Wynne’s articles on phenanthrene and quinoline for a new edition of Thorpe’s Dictionary of applied chemistry. Stimulated by his study of the relevant literature, and especially by Jackson & White’s synthesis of phenanthrene and anthracene from o-bromobenzyl bromide and Ullmann’s recently described synthesis of diphenyl by heating iodobenzene with copper powder, Kenner prepared 2:2'- ditolyl and thence, by side-chain bromination and debromination, dihydro- phenanthrene and phenanthrene. The availability of 2:2'-dibromoethyldiphenyl led him with Miss E. Turner (5) to study the formation and behaviour of seven- membered ring compounds such as the dibenzryc/oheptadienone (1).

The ease with which seven-membered rings could be formed from derivatives of 2:2'-ditolyl led him to a general discussion of the structure of diphenyl and its derivatives in one paper published in 1913 and a second with Miss A. M. Mathews (later to become Mrs Kenner) in 1914 on diphenyl-2:3:2':3'-and 3:4:3':4'-tetracarboxylic acids. In place of structure (2) Kaufler {Ann. 1907, 351, 152) had suggested (3) for diphenyl largely to explain the alleged existence of cyclic derivatives of benzidine such as (4). A study of anhydride formation from, and esterification of, the tetracarboxylic acids led Kenner & Mathews to the view that the Kaufler structure was most unlikely to represent diphenyl except, perhaps, transiently in exceptional circumstances; they did, however, consider it possible that the two rings in diphenyl might not be coplanar.



It was at this point that war broke out and Kenner joined the Army, rising to the rank of captain in the York and Lancaster Regiment. He was recalled from active field service in 1915 to take part in the production of chemical warfare agents. In his memoirs he records that his first assignment, and at the same time his first experience of chemical manufacture, was the production of liquid hydrogen sulphide at the works of Chance & Hunt Ltd at Oldbury, using a liquid air plant which had been requisitioned from Walsall. The plant was evidently badly designed and developed all kinds of faults during its operation so that he later described his time at Oldbury as giving him ‘six months of valuable experience at great national expense’. Thereafter he was drafted to manufacture phosgene, first at Calais and later at Lyon and Paris, using chlorine supplied from Runcorn, and to superintend the filling of Stokes bombs and other weapons with liquid phosgene. He returned to England in 1918 and until the end of the war acted as inspector of various chemical defence factories. In 1918 he married his former student Miss Annie Moore Mathews and in 1919 returned to academic work in Sheffield as lecturer in chemistry; there he resumed his study of aromatic nitro-compounds.

The availability of 2-iodo-3-nitrobenzoic acid prepared in the course of this work led Kenner & Stubbings (1921) to synthesize from it 6:6'-dinitrodiphenic acid. Their acid was not identical with the /3-dinitrodiphenic acid isolated by Schulz {Ann. 1880, 203, 95) as one of the nitration products of diphenic acid and apparently very fully characterized as the 6:6'-dinitro-acid by Schmidt & Kampf {Ber. 1903, 36, 3745) who claimed to have prepared 6:6'-dinitro-diphenyl from

392 Biographical Memoirs

COOH COOH COOH N 0 2ooN 0 2 COOH

6 ; y-acid

COOH

N 0 27



it by distilling its barium salt and carbazole by a like process from the corresponding diamino-acid. The acid of Kenner and Stubbings yielded on reduction a diamino-acid from which not carbazole but a tetracyclic diamide was obtained. They drew the conclusion that they were dealing with stereoisomers and formulated the /3-acid of Schulz as (5) their acid being allotted structure (6) and described as the y-acid. Whether the isomers should be regarded as having Kaufler structures or structures of the classical type was specifically left open.

In the following year (1922) Christie & Kenner (25) published a paper which broke new ground in stereochemistry. Discussing the stereoisomeric /3- and y- forms of 6:6'-dinitrodiphenic acid they pointed out that (i) on a planar formula for the diphenyl system neither form should be resolvable into optically active components; (ii) on the Kaufler formula or any similar one in which the planes of the two benzene nuclei are not parallel but equally inclined to a third plane, whereas the /3-compound would have a plane of symmetry, the y-isomer (7) would not be superimposable on its mirror image and should therefore be resolvable; (iii) ‘another possibility—and one at first sight perhaps more acceptable from the point of view of strain on the carbon atoms by which the two nuclei are united—is that the two benzene nuclei possess a common axis but do not lie in the same plane (8). In this case it will be seen that both forms of the acid should be resolvable. The limiting case of this kind, in which the planes of the two nuclei are at right angles, is at once excluded since it allows the existence of only one form of 6:6'-dinitrodiphenic acid.’

Christie & Kenner then resolved their y-dinitrodiphenic acid and also 4:6:4':6'-tetranitrodiphenic acid into enantiomorphic forms via their brucine salts. This left only (ii) and (iii) as possibilities and further evidence in favour of a non-planar structure was obtained by the resolution of 4:6:4'-trinitrodiphenic acid by the same authors in 1923 while the resolution of 6:6'-dichlorodiphenic acid by Christie, James & Kenner (31) showed that the asymmetry could not be due to any specific attribute of the nitro-group. Already in their 1922 paper Christie & Kenner (25) had observed that further nitration of both /3- and y- dinitrodiphenic acids gave one and the same 4:6:4':6'-tetranitro-acid; they record, too, in their 1923 communication (34), that the supposed 4:5-dinitro- phenanthraquinone from which, by oxidation, Schmidt & Kampf (loc. cit.) had obtained their /3-6:6'-dinitrodiphenic acid, yielded on further nitration and oxidation only 4:6:4'-trinitrodiphenic acid.

The complete solution of the problem of asymmetry was delayed for some time, partly because of the confusion which was now evident in the literature on diphenyl derivatives, and partly because of Kenner’s move to Australia in 1924. The friction between him and Wynne, already apparent before the war, became in Kenner’s view insupportable after his return to Sheffield and he determined to take the first opportunity to move; so it was that in 1924 he applied for and was appointed to the Chair of Organic Chemistry (Pure and Applied) in the University of Sydney. This move inevitably disrupted his researches, and, although the work was carried out with his students in Sheffield, it was not until early in 1926 that his next two papers in the series were published (Christie

James Kenner 393



& Kenner (34), Christie, Holderness & Kenner (35)). In these it was established that the jS-dinitrodiphenic acid of Schulz was not, as Schmidt & Kampf {loc. cit.) had alleged, 6:6'-dinitrodiphenic acid but instead 4:6'-dinitrodiphemc acid and that, moreover, like the 6:6'-isomer (the y-acid of Kenner & Stubbings) it was resolvable. Meanwhile Kenner’s outstanding work had been recognized by his election to the Fellowship of the Royal Society in 1925.

At this stage enough evidence was available to have permitted a full explanation of the optical activity of 2:2'-diphenic acids bearing at least one nitro-group in the 6(6')-positions. Yet although the true explanation—disymmetry due to restricted rotation about the pivot bond caused by interference between bulky groups in the o-positions—stems entirely from Kenner’s work it was in fact first formally advanced in November 1926 nearly simultaneously by Turner & Le Fevre ( C h e r n y . Ind. 1926, 45, 831, 883), by Bell & Kenyon {ibid. 1925, 45, 864) and, most succinctly, by Mills {ibid. 1926, 45, 884). It is the writer s belief that the real credit for the discovery of restricted rotation as a cause of dyssym- metry ought to go to Kenner and that he was forestalled in the formal statement of it by a combination of unfortunate circumstances. During his lifetime Kenner deposited in the archives of the Royal Society a collection of autobiographical notes together with a number of letters and other papers. Among them are two manuscripts of great interest. The first is a handwritten report by H. J. Hartley on the work carried out by him under Kenner’s supervision as Alfred Tongue Scholar at Sheffield during the academic year 1923-24. This is accompanied by a letter sent by Hartley to Sydney; the date of the letter (25 July 1924) together with internal evidence indicates that it was despatched while Kenner was aboard ship and it presumably reached him shortly after his arrival in Australia. In his letter Hartley states that ‘Prof. Wynne has kindly promised to forward my report to you now it is completed. He wished to see it again as, at the time at which it was due, the work was unfinished.’ It is therefore not clear when Kenner actually received the manuscript but it may well have been early in 1925. In this manuscript Hartley records that it was the opinion of Christie and Kenner that in the optically active diphenyl derivatives the two rings have a common axis but are not coplanar; he then points to the earlier demonstration by Graebe {Ann. 1888, 247, 258) that the two nuclei can move independently about their common bond and says that ‘possible attractions between the groups in the 2:2'- and 6:6'-positions together with steric effects may combine to prevent this independent rotation to a greater or lesser extent’. He then quotes Traube’s results {Ber. 1895, 28, 2728) showing that the various substituents in the 2:2'- and 6:6'-positions of the resolvable compounds all have fairly large molecular volumes (carboxy 20.8, nitro 21.7, methoxy 21.5, chlorine 13.2). Despite the smaller size of the chloro-substituents he was able to show that 2:2,-dichloro- 6:6/-dinitro-4:4,-diphenic acid could be resolved via its quinine salt but, as expected, the resolved acids showed a marked tendency to racemize. One must assume that the results of the work on j8-dinitrodiphenic acid by Christie and Holderness in Sheffield did not become available to Kenner until some time after Hartley’s findings; once they did, a less meticulous chemist than Kenner would




probably have propounded the restricted rotation theory but, characteristically, he seems to have been determined to remove every shadow of doubt by a few further experiments. To do these, and to consolidate work at Sheffield, still in part unfinished, must have been very difficult in the circumstances of the move to Sydney. Upon arrival there Kenner had not only to find a house for his family but was faced with the need to give a course of first-year lectures to a class of over 300, a type of teaching of which he had no previous experience. In addition he found himself President of Section B of the Australian Association for the Advancement of Science as its forthcoming meeting in Perth, and had also to serve on the New South Wales Committee of the reconstituted Australian equivalent of the British Department of Scientific and Industrial Research. The situation was not made any easier by the fact that he had only two research students, one of whom (V. M. Trikojus) left within the year to work at Oxford. Late in 1925 he, with V. M. Trikojus, submitted a memoir to the Chemical Society describing the resolution of 2-nitro-6:6'-diphenic acid and reporting their inability to resolve either 4-nitro-6:6'-diphenic acid or 4:4/-dinitro-6:6'- diphenic acid. The manuscript of this paper is now in the archives of the Royal Society together with a letter of rejection from the then editor of th ofthe Chemical Society and the negative reports he had received from two unnamed referees. These reports rested upon alleged incomplete characterization of the optical enantiomers and suggested the need for more work on attempted resolution of the 4-nitro- and 4:4'-dinitro-6:6'-diphenic acids! No doubt there was some justice in the comments about characterization but, even if incomplete, the wrork provided indubitable evidence of the resolvability of 2-nitro-6:6'- diphenic acid (a more complete resolution of this acid was later published by Bell & Robinson in 1927). This rejection so incensed Kenner, that according to his own account, he determined not to submit Hartley’s work to th ofChemical Society. So arose the hiatus in Kenner’s 1926 publications and the way was left open for the formal explanation of his results to be given in November of that year by others. There is no doubt that Kenner was deeply hurt by this outcome, and it is at least possible that his feeling of injustice played a part in the difficulties he was shortly to encounter in England.

In 1927 F. L. Pyman resigned from the Chair of Technological Chemistry at the Manchester College of Technology in order to join Boots Pure Drug Co. Ltd and, following strong pressure from Arthur Lapworth, then occupying the University Chair of Chemistry, Kenner applied and was appointed Pyman’s successor. It is open to question whether he would have applied without pressure from Lapworth amounting to a virtual invitation but, quite apart from the temptation to return to England for personal and domestic reasons, he had, as a result of his wartime experience, developed a strong desire to reform the teaching of applied chemistry in England, believing it to have so neglected the fundamentals of chemistry that it produced technicians rather than technologists; the Manchester Department as advertised embraced a variety of sections dealing with applied aspects of chemistry and must therefore have had some appeal. In the event, the move was a bitter disappointment to Kenner; upon his arrival

James Kenner 395



in Manchester in January 1928 not only did he find the conditions and facilities in the College of Technology far below his expectations, but it also transpired that a move to separate some of the important applied sections (notably textile chemistry) from his charge and set them up as an independent department was already under way. This action, of which Kenner had not been informed, had already been approved by the then Principal of the College, and, doubtless still smarting from his recent research experience, Kenner felt he had been duped and betrayed. No doubt there were rights and wrongs on both sides, but Kenner was never a man to take what he regarded as injustice lying down. Although he could not prevent the proposed changes, the ensuing battle so embittered relations between him and the College authorities that he reduced his contact with them to the minimum consistent with his occupancy of the Chair, and maintained his stance until his retirement in 1950. True, he did much to remould the teaching of applied chemistry in his own department; he introduced an undergraduate course in chemical engineering (the first of its nature in the country) and did much for the development of that subject in Manchester, but his refusal to cooperate with the other ‘applied’ departments of which he disapproved was to the considerable disadvantage of all concerned.

Despite the strained relations in Manchester Kenner pressed on with his researches. His sojourn in Sydney had lasted a bare three years and the difficulties of settling in and of developing research on a very narrow base were formidable. It is therefore not surprising that only a few publications—notably with H. E. Dadswell and with J. C. Earl who was later to succeed him in the Sydney Chair—stem from work actually done or initiated there. The most interesting of these are four papers in which Earl figures as a co-author; they are devoted to the chemistry of nitroso-compounds and led to later work in Manchester with, inter alia, E. C. S. Jones and D. W. Adamson. The initial stimulus to this work seems to have come from a disagreement with the view of Ingold 1925, 127, 513) that the ortho-para directive effect of the nitroso-group in benzene derivatives favoured Fliirscheim’s theory rather than that of Lapworth and Robinson. In one of these papers Earl & Kenner (42) showed that, since all nitroso- compounds liberate iodine from hydrogen iodide, the nitroso-group should be like halogen or hydroxyl in its directive effect. In a second paper (43) they studied the recovery of pinene from its nitrosochloride by treatment with aniline and discussed the concomitant formation of diazoaminobenzene. The tendency of the nitroso-group to pass into the wo-nitroso form was shown in the third paper (Earl, Ellsworth, Jones & Kenner (48)) to account for the success of the glycerol synthesis due to Piloty & Ruff ( . 1897, 30, 1656), and the sametendency was noted in a fourth paper in which oximes underwent transient conversion to nitroso-compounds during nitration (Charlton, Earl, Kenner & Luciano (56)). The elimination of aldehydes from the a-position in such compounds as (CH2OH)3C.NHOH on oxidation thus enabling nitroso-compounds to pass into the oximino-form was later extended (Jones & Kenner 1930) to instances of the transition of PhN = N — groupings to PhNH—N = again with extrusion of an a-hydroxylated carbon as aldehyde. Efforts to extend this type of




reaction to the synthesis of polyhydroxylic compounds related to carbohydrates were, however, unsuccessful (Charlton & Kenner (58)).

The further development of work on nitroso-compounds represents the most substantial single area of research exploited by Kenner during the 22 years he held the Manchester Chair. In 1928 Jones & Kenner (40) showed that a solution of cuprous chloride in hydrochloric acid will regenerate amines from nitrosamines and, following up their studies on the transition of nitroso- into oximino-compounds they examined (1933) a series of open-chain nitroso- compounds (9) derived from the addition products of mesityl oxide and primary amines. These underwent catalytic decomposition with alkali, and in the case of the product (9; R = Ph) from aniline a diazo-solution was obtained from which benzeneazo-/3-naphthol could be prepared by coupling. It was noted too that

Me2C-CH2COMe Me2C=CH-COMeI ----------> +

R-N-NO R-N=N-OH9

from (9; R = Me), diazomethane was formed by further decomposition and in cases where R represented a higher alkyl group olefines and alcohols were produced, presumably by breakdown of the transiently formed diazoalkane. This reaction was further studied by Adamson & Kenner (65) who showed that the decomposition products from the aliphatic diazo-compounds formed in the above reaction consist of a mixture of primary and secondary alcohols with olefine identical with that obtained by direct interaction of the primary amine and nitrous acid; it followed that the initial reaction of aliphatic primary amines with nitrous acid is one of diazotization. It was further shown (72, 81) that decomposition of the generally stable nitroso-compounds (9) derived from mesityl oxide with sodium Aopropylate or benzylate or with the sodium derivative of cyc/ohexanol provides an excellent preparative route to diazoalkanes in general. The accessibility of these latter compounds by this route led the same authors in 1939 to extend the observations of earlier workers on the conversion of carbonyl compounds to their homologues with diazomethane and to achieve in this way ring enlargement of cyc/ohexanone and cyc/oheptanone (83).

For the rest, Kenner’s work in the Manchester College of Technology is described in a number of papers dealing with a variety of rather disparate topics most of them having a theoretical interest although a few, such as those with Morton (84) and Wain (85) on the formation of ketones from acids, were directed to improving experimental methods. Among those more theoretically oriented is a substantial group with G. Baddeley dealing inter alia with such topics as anomalous m-substitution in benzene derivatives (1935), on the kinetics of sulphonation and desulphonation (Baddeley, Holt & Kenner (90)), and the rearrangement of acyldiazoalkanes (96). World War II naturally restricted his activities but towards its end he argued (91, 92) for the general expression of all chemical reactions in terms of oxidation and reduction and elaborated his view further in a paper with Baddeley & Graddon (94) on the oxidation of 4:4'-diethoxydinaphthyl.

James Kenner 397



The latter part of Kenner’s tenure of the Manchester Chair was marred by domestic tragedy. As already mentioned, he married in 1918 his former student and collaborator in research, Annie Moore Mathews, the daughter of a well known general medical practitioner in Sheffield. There were two sons of the marriage, Donald James born in 1919, who graduated in mechanical engineering at Manchester University, and George Wallace born in 1922, who studied chemistry, is now Heath Harrison Professor of Organic Chemistry in the University of Liverpool, and was elected a Fellow of the Royal Society in 1964. The quiet, closely knit family was a source of stability and strength to Kenner in all his difficulties. He had few interests outside his chemistry but found recreation in walking or cycling in the countryside around Manchester at week-ends or on holiday in the southwest of England. On one of these excursions in September 1943 Mrs Kenner was killed in a cycling accident and later in the same month came the news that their elder son Donald had been killed in action at Salerno in Italy. Kenner’s reaction to this appalling double blow was to plunge more deeply than ever into his work, but his loneliness was apparent to his friends during the remainder of his association with the College of Technology.

Immediately following his retirement in 1950 Kenner was invited by his former Sheffield student J. Wilson, now Director of the recently formed Rayon Research Association, to join in the research work of the Association at its Heald Green Laboratories on the southern outskirts of Manchester. Here he threw himself heart and soul into what was, for him, the new field of carbohydrate chemistry. He quickly made substantial contributions to our knowledge of the action of alkali on carbohydrates and especially to our understanding of the so-called ‘tendering’ of cotton fabrics which he showed was due to photooxidation of cellulose followed by degradation of the fibre by the action of alkali during washing. The reaction involved in the breakdown was shown to be essentially that which occurs between /3-alkoxyketones and alkali:

^CHOR—CHX—CO— -------- > —CH=CX—CO + R-OH

In the carbohydrate series the products of reaction are the saccharinic acids whose importance to the understanding of carbohydrate chemistry had, in Kenner’s view, been largely overlooked by the classical schools of carbohydrate chemistry—a view which he expressed in characteristically forthright terms. The period at Heald Green was one of the most productive in Kenner’s research career; his work on the action of alkali on carbohydrates is described in some 15 papers in th & Journal of the Chemical Society between 1953 and 1957 and in a number of other publications; he published a comprehensive review of much of this work in Chemistry and Industry (112). The carbohydrate papers represent perhaps the most coherent group published by Kenner subsequent to his diphenic acid work, and the fact that they rest on work done after his formal retirement suggests that his overall contribution to chemistry might have been greater had his stay at the Manchester College of Technology been free from the controversies and sterile disputes which were such prominent features of it.




399

Throughout his career James Kenner was something of a stormy petrel and there is no doubt that he was regarded by many of his contemporaries as aggressive and quarrelsome in some of his dealings with others. Yet it seems to the writer that this view does not quite fit with the impression he made on the relatively few who knew him well. Always intolerant of the shoddy or mediocre and given to rather hasty judgements, he certainly became embroiled in many bitter disputes, some of which could, with tact, have been avoided. He was, however, a very shy person at heart and, like many shy people, he sought to conceal his shyness behind a stern appearance and a brusque manner which, in his later days at least, was liable to produce an initial reaction of fear rather than one of affection in his younger students. This unusual mixture of sensitivity and intolerance which determined so much of his behaviour is well illustrated in his experiences at the University of Sydney. On his arrival there, without taking time to learn something of a milieu with which he was unfamiliar, he immediately set about complete revision of the first-year teaching. As a result he was soon at loggerheads with both senior staff and students—with the former because he regarded their standard as mediocre and said so, and with the latter because he was too sensitive to tolerate barracking by the robust and outspoken post-war generation of Australian students. And yet J. C. Earl, lecturer when Kenner arrived and later to succeed him as professor, gained and retained his fiiendship and still speaks of him with affection and with the respect due to one who, whatever his faults, did much during his stay for organic chemistry in Sydney. V. M. Trikojus, later Professor of Biochemistry in the University of Melbourne, was one of his research students in Sydney and always speaks with gratitude of the friendship and help he received from Kenner at the outset of his career.

Much later when the author of this memoir went to the University of Manchester in 1938 as a young and totally inexperienced Professor of Chemistry he came to know Kenner well and found him both a good and helpful friend, always ready to offer advice when it was requested, and showing no apparent resentment when it was rejected. Not that Kenner’s advice was usually unsound —far from it—for he had a remarkable feeling or flair for organic chemistry. This apparent flair was doubtless a reflection of his wide knowledge of the chemical literature of which he was a voracious reader. In disputes he was a ‘bonnie fechter’ and he dearly loved an argument on theoretical matters. As far back as 1932 he entered the lists against the theory of enzymic oxidation of alcohol to acetaldehyde due to Haber & Willstatter (Ber. 1931, 64, 2844) on the grounds that the mechanism proposed was contrary to general organic chemical experience. During his period at the Rayon Research Association Laboratories he returned to the attack on the hydrogen-abstraction theory of the photooxidation of alcohol (117, 118) and this initiated a polemical correspondence with the physical chemists (of whom as a whole he had no great opinion) which he continued almost unabated and with evident enjoyment long after his final retirement. Kenner’s love of dispute extended well beyond science. As already mentioned, he had few interests beyond his family and chemistry but one of them was cricket. He returned from Sydney a devoted admirer of Australian cricket.

James Kenner



Professor Frank Morton, one of his students in Manchester (and later to become Professor of Chemical Engineering), tells how he was once invited to accompany Kenner to a Test Match against Australia at Old Trafford in the year of Wood- full’s captaincy when Bradman was at his peak. Somewhat to Morton s surprise they went into the standing accommodation where they were surrounded by solid north-country supporters of the M.C.C. Those who knew him will, perhaps, not be surprised to learn that Kenner revealed himself as a rabid Australian supporter who proceeded to inform his neighbours in forthright terms about the deficiencies of the English team and what the Australians would do to them. It must have been a lively afternoon!

During his lifetime James Kenner had his detractors and no doubt he brought at least some of his troubles on himself by his intolerance of what he believed to be second-rate. But this should not blind us to his ability or to the respect in which he was held by those who worked with him; nor should we forget either his kindliness or the friendship and help he gave freely to those who, like the author of this memoir, were his younger colleagues. And the discovery of optical isomerism due to restricted rotation which stands to his credit is certainly an achievement which will ensure for the name of James Kenner a permanent and well deserved place in the annals of organic chemistry.

The author wishes to record here his gratitude to former students and associates of James Kenner—especially Professor J. C. Earl and Professor Frank Morton—and to his son Professor G. W. Kenner for providing him with much valuable information.

The photograph is by Mrs Lotte Meitner-Graf.


(1) 1904

(2) 1907

(3) 1908

(4) 1910

(5) 1911

(6) 1912

(7)

(8) 1913

(9)

(10) 1914

( 11)

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(With E. K noevenagel) Zur Darstellung von Sulfinsauren. Ber. chem. Ges. 41, 3315-3322.

(With E. W itham) The formation of tolane derivatives from p-chloro- toluene and 3:4 dichlorotoluene. J.Chem. Soc. 97, 1960—1967.

(With E. G. T urner) Formation of six- and seven-membered rings from derivatives of 2:2/-ditoyl. J.Chem. Soc. 99, 2101-2114.

Diphenyl-2:3:2':3'-tetracarboxylic acid. Preliminary note. Proc. Chem. Soc. 28, 277.

(With E. G. T urner) The reactions of dibenzocycloheptadienone. Preliminary note. Proc. Chem. Soc. 28, 277.

(With E. W itham) 2:2, :Ditolyl-5:5'-dicarboxylic acid. Chem. Soc. 103, 232-238.

The formation of cyclic compounds from derivatives of 2:2'-ditolyl. J. Chem. Soc. 103, 613-627.

(With R. Curtis) The condensation of ethyl glutaconate. J. Chem. Soc. 105, 282-290.

(With A. M. M athews) 2-hydrindamine. J. Chem. Soc. 105, 745-748.



(12) 1914 (With A. M. M athews) Diphenyl-2:3:2,:3,-and-3:4:3':4,-tetracarboxylicacids. J. C h a n . Soc. 105, 2471-2482.

(13) (With J. H. H adfield) The preparation of 3-nitro-o-toluidine. Proc.Client. Soc. 30, 253-254.

(14) The reduction products of ethyl hydrindene-2:2-dicarboxylate. J. Chem.Soc. 105, 2685-2697.

(15) The influence of nitro-groups on the reactivity of substituents in thebenzene nucleus. D.Sc. Thesis, London.

(16) The influence of nitro-groups on the reactivity of substituents in thebenzene nucleus.^. Chem. Soc. 105, 2717—2738.

(17) 1920 (With C. W. James & W. V. Stubbings) Note on the preparation ofcertain iodo-compounds. J.Chem. Soc. 117, 773-776.

(18) (With M. Parkin) The influence of nitro-groups on the reactivity of substituents in the benzene nucleus. II. The dinitrotoluenes. Chem. Soc.117, 852-859.

(19) 1921 (With W. V. Stubbings) A second form of 6:6'-dinitrodiphenic acid, andits conversion into new cyclic systems.^. Chem. Soc. 119, 593-602.

(20) (With H. Burton) The influence of nitro-groups on the reactivity of substituents in the benzene nucleus. III. The partial reduction of the dinitrotoluenes by stannous chloride and hydrochloric acid. J. Chem. Soc. 119, 1047-1053.

(21) (With E. Witham) The influence of nitro-groups on the reactivity of substituents in the benzene nucleus. IV. The condensation of ethyl 3- and 5- nitro-2-chlorobenzoates with hydrazines.^. Chem. Soc. 119, 1052-1058.

(22) (With E. Witham) The influence of steric factors on intramolecularcondensation.^. Chem. Soc. 119, 1452—1461.

(23) 1922 (With H. Burton) The influence of nitro-groups on the reactivity of substituents in the benzene nucleus. V. Heteronuclear dinitro-derivatives.

J.Chem. Soc. 121, 489-496.(24) Configurations of molecules of benzenoid substances. Nature, Lond. 109,

581.(25) (With G. H. Christie) The molecular configurations of polynuclear aro

matic compounds. I. The resolution of y-6:6'-dinitro- and 4:6:4':6'- tetranitrodiphenic acids into optically active components. J. Chem. Soc. 121, 614-620.

(26) (With H. Burton) The influence of nitro-groups on the reactivity ofsubstituents in the benzene nucleus. VI. The elimination of halogen during the reduction of halogenated nitro-compounds. J. Chem. Soc. 121, 675-682.

(27) 1923 Stereoisomerism among derivatives of diphenyl. Nature, Lond. 112, 539—540.

(28) (With G. H. Christie) The molecular configurations of polynuclear aromatic compounds. II. 4:6:4/-trinitrodiphenic acid and its resolution into optically active components. J.Chem. Soc. 123, 779-785.

(29) (With H. Burton) The molecular configurations of polynuclear aromaticcompounds. III. Diphenyl-S^S'^'-tetracarboxylic acid. J . Chem. Soc. 123, 1043-1045.

(30) (With K. Ibbotson) The influence of nitro-groups on the reactivity ofsubstituents in the benzene nucleus. VII. Reactions of 2:5- and 4:5- dinitro-m-xylenes. J.Chem. Soc. 123, 1260-1268.

(31) (With G. H. Christie & C. W. James) The molecular configurations ofpolynuclear aromatic compounds. IV. 6:6'-dichlorodiphenic acid; its synthesis and resolution into optically active components. J. Chem. Soc. 123, 1948-1951.

James Kenner 401



402(32) 1923

(33) 1925

(34) 1926

(35)

(36)

(37)

(38) 1927(39)

(40)

(41)

(42)

(43)

(44) 1928

(45)

(46)

(47)

(48)

(49)

(50) 1930(51)

(52) 1931

(53)

(54)

(55)

(With F. A llsop) The relationship of the tautomeric hydrogen theory to the theory of induced alternate polarities. Chem. Soc. 123, 2296-2315.

(With C. W. T od & E. W itham) The influence of nitro-groups on the reactivity of substituents in the benzene nucleus. VIII. 2:3- and 2:5- dinitro-p-chlorotoluenes. jf.Chem. Soc. 127, 2343—2349.

(With G. H. Christie) The molecular configurations of polynuclear aromatic compounds. V. The identity of the nitration products derived from 2:7- and 4:5-dinitrophenanthraquinones. Chem. Soc. 470-476.

(With G. H. Christie & A. H olderness) The molecular configurations of polynuclear aromatic compounds. VI. fi-Dinitrodiphenic acid; its constitution and resolution into optically active components. J. Chem. Soc. 671-676.

(With H. Burton & F. H ammond) Mercuration of o-nitrotoluene. Chem. Soc. 1802-1804.

Some aspects of the problem of molecular structure. Presidential address. Rept. Auts. Assn Adv. Science 18, 132-155.

The space formula of diphenyl. Cherny Ind. 46, 218-220.(With H. E. D adswell) The influence of nitro-groups on the reactivity

of substituents in the benzene nucleus. IX. 2:3- and 2:5-dinitro-4- methoxytoluenes. J. Chem. Soc. 580—588.

(With H. E. D adswell) The basic character of the acetoxylidides and its influence on the course of their substitution.^. Chem. Soc. 1102-1108.

(With J. W ilson) Jackson and White’s synthesis of phenanthrene.J.Chem. Soc. 1108-1112.

(With J. C. Earl) The recovery of pinene from its nitrosochloride. Chem. Soc. 1269-1276.

(With J. C. Earl) The action of hydrogen iodide on nitroso compounds. J. Chem. Soc. 2139-2145.

(With J. G. Jackson) A contribution to the stereochemistry of tervalent nitrogen. .7. Chem. Soc. 573-581.

(With J. G. Jackson) a:y-Diamino-(i-phenylpropane and related compounds of pharmacological interest.^. Chem. Soc. 1657-1662.

(With F. B. M cA lister) The molecular configurations of polynuclear aromatic compounds. VII. 5:5'-Dichlorodi phenyl-3:3'-dicarboxylic acid. J.Chem. Soc. 1913-1916.

(With H. A. T urner) The molecular configurations of polynuclear aromatic compounds. VIII. 6:6'-Dimethoxydiphenic acid. J. Chem. Soc. 2340-2343.

(With J. G. Earl, F. C. Ellsworth & E. C. S. Jones) A contribution to the chemistry of nitroso compounds.^. Chem. Soc. 2697-2703.

Bemerkung zu der Abhandlung von J. Boeseken und B. B. C. Felix: Uber die Konfiguration des Penterythrits, II. Mitteilung: Die optischaktiven Di-benztraubensaure-penterythrite. Ber. Deutschen Chem. Ges. 61, 2470-2471.

Resolution of cyclic azoxy compounds. Cherny Ind. 49, 397.(With E. C. S. Jones) The action of benzenediazonium chloride on

(3-nitroethyl alcohol and its derivatives. X Chem. Soc. 919-928.(With H. Shaw) A synthesis of unsymmetrical diphenyl derivatives.

J.Chem. Soc. 769-773.(With E. C. S. Jones) The direct formation of quinones from 2:6-disub-

stituted derivatives of 4-nitrophenol. Jf.Chem. Soc. 1842-1857.(With E. C. S. Jones) The interaction of 2:6 dichloro-4-methylquinitrol

with methyl and ethyl alcohols. ^ Chem. Soc. 1943-1950.An aspect of co-ordination. Nature, Lond. 128, 1000-1001.




James Kenner 403

(56) 1932

(57)

(58)

(59)

(60)

(61) 1933

(62) 1934

(63)

(64)

(65)

(66)(67) 1935

(68)

(69)

(70)

(71)(72)

(73) 1936

(74)

(75)

(76)

(77)

(78) 1937

(79)

(80)

(With W. Charlton, J. C. Earl & A. A. L uciano) The nitration of oximes. J. Chem. Soc. 30-41.

(With E. C. S. Jones) The analogy between the benzidine change and the dissociation of oxides of nitrogen. A new reagent for the recovery of secondary bases from nitrosoamines and for purifying amines. J. Chem. Soc. 711-715.

(With W. Charlton) Experiments on the synthesis of polyhydroxylic compounds.^. Chem. Soc. 750-755.

Zur Theorie der Oxydationsprozesse; Bemerkungen zu der Abhandlung von F. Haber und R. Willstatter: ‘Unpaarigkeit und Radikalketten in Reaktionsmechanismus organischer und enzymatischer Vorgange’. Ber dt. chem. Ges. 65, 705-710.

A correlation of the Walden inversion with the pinacone and Beckmann changes. Nature, Lond. 130, 309.

(With E. C. S. Jones) The catalytic decomposition of nitroso-(3-alkyl- amino-ketones. I. A new method of preparing diazomethane, and evidence of the occurrence of diazotisation in the aliphatic series. J. Chem. Soc. 363-368.

(With J. H annon) An instance of the action of air in determining the course of bromination. J. Chem. Soc. 138.

(With G. Baddeley) The oxidation of 4-n-propylphenol to 2-n-propyl- quinol. J. Chem. Soc. 633-634.

(With F. M orton) An instance of the reversed field effect of the methyl group. J.Chem. Soc. 679-680.

(With D. W. Adamson) The decomposition of the nitrites of some primary aliphatic amines. X Chem. Soc. 838-844.

Some aspects of the chemistry of nitrogen. Sci.y. Roy. Coll. Sci. 4, 54-59.(With M. Polanyi & P. Szego) Aluminium chloride as a catalyst of hydro

gen interchange. Nature, Lond. 135, 267-268.(With D. W. A damson) The preparation of diazomethane and its homo-

logues. y. Chem. Soc. 286-289.(With F. S. Statham) The constitution of apocinchene and syntheses of

its methyl and ethyl ethers.^. Chem. Soc. 299-303.(With G. Baddeley) The meta-alkylation of aromatic hydrocarbons by the

Friedel-Crafts reaction, y. Chem. Soc. 303-309.Formation of galactose in vital processes. Nature, Lond. 135, 506.(With D. W. Adamson) Preparation of diazomethane and its homologues

in the free state. Nature, Lond. 135, 833.(With F. S. Statham) Zur Darstellung der 4-Alkyl- und 4-Aryl-chinoline.

Ber. dt. chem. Ges. 69, 16-18.(With F. S. Statham) Zur Stereochemie des 3-wertigen Stickstoffs.

Ber. dt. chem. Ges. 69, 187-188.(With E. C. Knight) Zur Kenntnis der Osazon-Bildung. Ber. dt. chem.

Ges. 69, 341-343.(With B. K. N andi) Ein Struktur-Analogon des Cinchens und sein

Verhalten gegen Sauren. Ber. dt. chem. Ges. 69, 635-639.(With G. Baddeley) Zur Kenntnis des Crackverfahrens; pyrolytische

Umwandlung des p-Xylols in m-Xylol. Ber. dt. chem. Ges. 69, 902-904.Correlation of the yellow oxidation ferment with Warburg’s co-ferment.

Nature, Lond. 139, 25-26.(With W. H. R itchie & F. S. Statham) A synthesis of 5:6:7:8-tetrahydro-

phenanthridine and its derivatives.^. Chem. Soc. 1169-1172.(With W. H. Ritchie & R. L. W ain) A relationhsip between (3-naphthyl-

amine and (3-aminocrotonate. y.Chem. Soc. 1526-1529.



404(81) 1937

(82) 1938(83) 1939

(84)

(85)

(86) 1941(87)(88)(89) 1943

(90) 1944

(91) 1945(92) 1946(93)(94) 1947

(95)(96) 1949

(97) 1953

(98)

(99)

(100)

(101)

(102) 1954

(103)

(104)

(105)

(106)

(107)

(108)

(109) 1955

(110)

(With D. W. Adamson) Improved preparations of aliphatic diazo-compounds and certain of their properties.^. Chem. Soc. 1551—1556.

Formation of mesomeric systems. Nature, Lond. 141, 786-787.(With D. W. A damson) Reactions of aliphatic diazo-compounds with

carbonyl derivatives.^. Chem. Soc. 181—189.(With F. M orton) Umwandlung der Carbonsauren in Ketone mit Hilfe

ihrer Bleisalze. Ber. dt. chem. Ges. 72, 452—456.(With R. L. W ain) Thermische Zersetzung der Bleisalze einiger oc-Oxy-

carbonsauren. Ber. dt. Chem. Ges. 72, 456-459.A property of conjugated systems. Nature, Lond. 147, 482.Diazotisation. Cherny Ind. 60, 443-447.The carbonyls. Nature, Lond. 148, 345.The historical method in teaching science. Mem. Proc. Manchr Lit. Phil.

Soc. 85, 95-100.(With G. Baddeley & G. H olt) Relationship between sulphonation and

desulphonation. Nature, Lond. 154, 361.Oxidation and reduction in chemistry. Nature, Lond. 156, 369-370. Oxidation and reduction in chemistry. Nature, Lond. 157, 340.(With K. M ackay) Structure of the sydnones. Nature, Lond. 158, 909-910. (With G. Baddeley & P. G raddon) A semiquinonoid oxidation product

of 4:4'-diethoxy-l:l'-binaphthyl. Nature, Lond. 160, 187-188.(With K. M ackay) 1-Acylhydrazines. Nature, Lond. 160, 465-466.(With G. Baddeley & G. H olt) Rearrangement of acyldiazoethanes.

Nature, Lond. 163, 766-767.(With W. M. Corbett & G. N. R ichards) Carbonyl oxycelluloses. Cherny

Ind. 154.(With W. M. Corbett & G. N. R ichards) Carbonyl oxycelluloses. Cherny

Ind. 462.(With G. N. R ichards) The degradation of carbohydrates by alkali. I.

a-Alkoxy-ketones. J. Chem. Soc. 2240-2244.(With W. M. Corbett) The degradation of carbohydrates by alkali. II.

Lactose.^. Chem. Soc. 2245-2247.(With W. M. Corbett) Trans-esterification as a means of halide esteri

fication under neutral conditions.^. Chem. Soc. 3572-3575.(With G. N. Richards) The degradation of carbohydrates by alkali. III.

3-0-methyl derivatives of glucose and fructose.^. Chem. Soc. 278-282. (With G. N. R ichards) The degradation of carbohydrates by alkali. IV.

1 -0-methylfructose, glucose, and fructose.^. Chem. Soc. 1784-1789. (With W. M. Corbett) The degradation of carbohydrates by alkali. V.

Lactulose, maltose, and maltulose. jf.Chem. Soc. 1789-1791.(With W. M. Corbett) The degradation of carbohydrates by alkali. VI.

Laminaribiose and turanose. J.Chem. Soc. 3274-3277.(With G. N. Rihcards) The degradation of carbohydrates by alakli. VII.

5-0-benzyl and 3:5-0-benzylidene-2-deozy-D-ribose. J . Chem. Soc. 3277-3281.

(With W. M. Corbett) The degradation of carbohydrates by alkali. VIII. Melibiose. J.Chem. Soc. 3281-3283.

(With G. N. Richards) Alkaline degradation of amylose. Cherny Ind. 1483-1484.

(With W. M. Corbett) The degradation of carbohydrates by alkali. IX. Cellobiose, cellobiulose, cellotetraose, and laminarin. J. Chem. Soc. 1431-1435.

(With W. M. Corbett & G. N. Richards) The degradation of carbohydrates by alkali. X. Acetal derivatives.^. Chem. Soc. 1709-1711.




James Kenner 405(Ill) 1955

(112)

(113) 1956

(114)

(115)

(116)

1957

(117)(118) 1958(119) 1960(120) 1966(121) 1968

(With G. N. Richards) The degradation of carbohydrates by alkali. XI.4-0-methyl derivatives of glucose and fructose.^. Chem. Soc. 1810-1812.

The alkaline degradation of carbonyl oxycelluloses and the significance of saccharinic acids for the chemistry of carbohydrates. Chemy 727- 730.

(With G. N. Richards) The degradation of carbohydrates by alkali. XII. 6-0-methyl- and 3:6- and 4:6-di-0-methyl-D-glucose. Chem. Soc. 2916-2925.

(With G. N. Richards) The degradation of carbohydrates by alkali. XIII. 2:3-di-0-methyl-glucose and its conversion into 5-hydroxymethyl - furfuraldehyde. jf.Chem. Soc. 2921-2925.

(With W. M. Corbett) The degradation of carbohydrates by alkali. XIV.3:6-anhydro-D-glucose. J.Chem. Soc. 927-928.

(With G. N. R ichards) The degradation of carbohydrates by alkali. XV. Factors in the formation of metasaccharinic acids from 3-0-derivatives of glucose.^. Chem. Soc. 3019-3024.

Oxidation of alcohol. Nature, Lond. 179, 142-143.Some mechanisms of oxidation. Tetrahedron 3, 78-89.Further considerations on oxidative processes. Tetrahedron 8, 350-355. Formation of nitrous oxide. Nature, Lond. 212, 1461.Benzidine rearrangement. Nature, Lond. 219, 153.



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