Substitution, electrophilic of heterocycles

For monographs, see Taylor, R. Electrophilic Aromatic Substitution Wiley NY, 1990 Katritzky, A.R. Taylor, R. Electrophilic Substitution of Heterocycles Quantitative Aspects (Vol. 47 of Adv. Heterocycl. Chem.) Academic Press NY, 1990. For a review, see Taylor, R. in Bamford Tipper Comprehensive Chemical Kinetics, vol. 13 Elsevier NY, 1972, p. 1. 

Electrophilic substitution is much easier than in benzene. Thiophene reacts about as readily as mesitylene pyrrole and furan react as readily as phenol or even resorcinol. Electrophilic substitution of heterocycles has been reviewed (86HC(44/2)l), (90AHC(47)87), and the following conclusions were reached ... 

The final two chapters both deal with aspects of the electrophilic substitution of heterocycles. Derek T. Hurst of Kingston University (England) summarizes nitrations which occur in phenyl rings as substituents in heterocycles. Finally, we present the second of the three-part series by M. Ross Grimmett (also from the University of Otago) on the haloge-nation of heterocycles. This part deals with six-membered heterocycles. 

Katritzky, A. R, Taylor, R., Electrophilic Substitution of Heterocycles Quantitative Aspects, 47, 1. 

The heterocyclic literature is enormous, and a significant fraction deals with electrophilic substitution reactions of heteroaromatics. A great many authors have provided quantitative data, but the data are scattered through the literature, rarely reviewed comprehensively, and still less interpreted. Indeed, a proper interpretation is possible only by taking the wider view. This is what this book is intended to provide. It has been found possible not only to give interpretations of all of these quantitative data—in many cases for the first time—but to consider, additionally, much of the semiquantitative and qualitative work on the electrophilic substitution of heterocycles. 

Volume 47 of Advances in Heterocyclic Chemistry is, unlike most volumes, a monograph and deals with the quantitative aspects of electrophilic substitution of heterocycles. It is written by Roger Taylor of the University of Sussex, Brighton, England, and your editor with one chapter contributed by Ross Grimmett of the University of Otago in New Zealand. It is hoped that this survey of the whole area of electrophilic substitution of heterocycles, covering as it does semiqualitative as well as completely quantitative aspects, will be of considerable help to workers in the field. 

Katritzky AR, Taylor R (1990) Electrophilic substitution of heterocycles quantitative aspects. In Katritzky AR (ed) Advances in heterocyclic chemistry. Academic Press, San Diego... 

Electrophilic substitution of heterocycles, quantitative aspects 90AHC(47)1. 

Electrophilic substitution of thiophene has been expertly reviewed by Taylor <86HC(44/2)l>. In addition, a whole monograph has b n devoted to the compilation and analysis of quantitative data on electrophilic substitution of heterocycles <90AHC(47)87>. The highlights from the conclusions reached in the section on thiophene are presented below. 

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