Fluorinated Hete-rocyclic Compounds

The presence of one or morefluorine atoms in an organic mol-

ecule can have a dramatic effect onits physical and chemical properties. In

some cases reactivity can increase, inothers it may decrease, and some fluorinated

compounds are extremely stable and find appli-cations in materials science. Fluorine can alter theproperties of drug compounds increasing theirmetabolic stability and enhancing their activity,while the presence of fluorine can alter themechanistic course of many reactions leading tounexpected and intriguing behavior.

Organofluorine chemistry has become animportant discipline since the first major develop-ments of the subject in the 1960s, and the recentincreased availability of organofluorine compoundshas led to rapid advances in synthetic and materialsapplications. There are a number of recent goodbooks available on organofluorine chemistry, butthis work, edited by Viacheslav Petrov, is the firstmajor contribution devoted specifically to fluori-nated heterocycles. The already diverse propertiesand reactivity of heterocyclic compounds areincreased even more by the presence of fluorineatoms, and gives rise to a fascinating field ofsynthetic and mechanistic chemistry. This bookbrings together contributions from seventeen lead-ing researchers in heterocyclic fluorine chemistry,and covers in detail the chemistry of small,medium, and large ring compounds in ten chapters.A second part of the book, chapters 11–13, coverapplications of fluorinated heterocycles, specifi-cally agrochemicals, pharmaceuticals, and materialschemistry.

The first two chapters of Part I cover thechemistry of three- and four-membered hetero-cycles, including the key oxiranes, aziridines, oxe-tanes, thietanes, and some of their unsaturatedcounterparts. Their synthesis from fluoroalkenesprecursors is discussed. Chapter 3 describes thesynthesis, properties and reactions of the importantgroup of nitrogen containing five-membered ringcompounds, namely pyrrolidines and pyrroles, aswell as poly-aza, and fused-nitrogen-ring com-pounds. Interesting aspects of oxygen, sulfur,selenium, and phosphorus containing rings bearingfluorine are discussed in chapter 4 while carbohy-drate compounds are covered in chapter 5.

Six-membered fluorinated ring compounds areof major significance with pyridines being the moststudied, and are assigned three chapters of thebook. Chapter 6 discusses the introduction offluorine atoms selectively into pyridine derivatives,by among others, the Balz–Schiemann reaction andarene lithiation methods. Reactions of perfluoro-

pyridine including the important SNAr reactionswhich can lead to useful multifunctionalised pyr-idines (and other azaarenes) is covered largely inchapter 8, while chapter 7 discusses six-memberedheterocycles with fluoroalkyl side chains. Methodsand reagents for the introduction of fluoroalkylgroups are covered, as well as ring synthesis fromfluoroalkyl containing building blocks.

The “mirror image” nature of non-aromatic or“saturated” perfluoroheterocycles is described inchapter 9 and larger rings including and azepines,diazepines, oxazepines as well as fused rings, andmacrocycles are reviewed in chapter 10. Eachchapter is well written and clearly illustrated withgood reaction schemes that illustrate the diverse,intriguing, and often difficult to predict, reactionsthat fluorinated compounds undergo. There is awealth of fascinating chemistry presented.

Part II of the book consists of three chapters onimportant applications of fluorinated heterocyles.Chapter 11 describes recent advances in fungicidesand insecticides, while chapter 12 discusses fluo-rine-containing pharmaceuticals. The fact that 10%of all current drug compounds sold contain fluorineshows the important effect this element has onpharmacological properties. Discussion of the syn-thesis of key fluorine-containing antiviral andantibacterial drugs is presented as well as examplesof compounds which act against cancers, parasites,and neurological disorders. The final chapter dis-cusses materials applications with an emphasis onpolymers and oligomers derived from fluorinatedepoxides. These three chapters give a nice perspec-tive of the many important uses of fluorinatedheterocycles. The separation of the applicationsfrom the detailed chemistry of the various ringsystems emphasizes their growing importance.

The book is well referenced and indexed andcovers the literature from pioneering work in the1960s to recent developments up to 2009. Itprovides an excellent source of information onfluorinated heterocycles as well as something to dipinto if you are looking for some unexpected andstimulating chemistry. The book is suitable foradvanced undergraduates and research studentsand represents a valuable addition to the literaturethat should be on the shelves of libraries in bothacademic and industrial institutions. I would rec-ommend this book to all scientists who considerworking with fluorinated compounds—be theysynthetic chemists, life-science chemists, or materi-als scientists.

George WeaverDepartment of Chemistry,Loughborough University (England)

DOI: 10.1002/anie.201003132

Fluorinated HeterocyclicCompoundsSynthesis, Chemistry andApplications. Edited byViacheslav A. Petrov. JohnWiley & Sons, Hoboken2009. 516 pp., hardcover,E 105.00.—ISBN 978-0470452110

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