A re-evaluation of the electrophilic substitution reactions of the Ramirez ylide

LJ Higham, J Muldoon, PG Kelly, DM Corr…

Index: Higham, Lee J.; Kelly, P. Gabriel; Corr, David M.; Mueller-Bunz, Helge; Walker, Brian J.; Gilheany, Declan G. Chemical Communications, 2004 , # 6 p. 684 - 685

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Citation Number: 5

Abstract

Cyclopentadienylidenetriphenylphosphorane (the Ramirez ylide), unexpectedly and contrary to a number of earlier reports, has been shown to be like pyrrole in undergoing electrophilic substitution on the cyclopentadienide ring at either the 3-or the 2-position, depending on the electrophile. Formylation under Vilsmeier conditions and addition of tetracyanoethylene occurs at the 3-position, while activated acetylenes and the nitrosyl ...