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Nucleophilic Reactivities of Pyrroles (Eur. J. Org. Chem. 14/2008)
Author(s) -
Nigst Tobias A.,
Westermaier Martin,
Ofial Armin R.,
Mayr Herbert
Publication year - 2008
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200890033
Subject(s) - nucleophile , electrophile , chemistry , pyrrole , alkyl , medicinal chemistry , substitution reaction , computational chemistry , stereochemistry , organic chemistry , catalysis
The cover picture is misleading! With the determination of the nucleophilic reactivities of pyrroles, our electrophilicity‐nucleophilicity puzzle, where synthetically useful reactions are found in the green corridor (see: R. Lucius, R. Loos, H. Mayr, Angew. Chem. Int. Ed. 2002 , 41 , 91–95), is not yet complete. The picture illustrates, however, that the reactions of pyrroles with electrophiles also follow the linear free‐energy relationship log k 20°C = s ( N + E ), where N and s characterize the reactivities of nucleophiles and E describes the reactivities of electrophiles. Alkyl substitution increases the nucleophilicity of pyrrole by a factor of up to 10 million, and from the nucleophilicity parameters reported in this article by H. Mayr et al. on p. 2369 ff, one can derive suitable electrophilic reaction partners for alkyl‐substituted pyrroles.