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

Lookup NU author(s): Dr Lee Higham

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Abstract

(Chemical Equation Presented) 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 electrophile substitute at the 2 position. The 3-formylated product was reduced to the 3-methyl derivative and it also reacted under Knoevenagel conditions to give a number of novel condensation products. The results of single-crystal X-ray crystallographic analyses are given for four of the compounds studied, and a careful 2D NMR analysis of all of the compounds was performed in order to develop a reliable method for the unambiguous assignment of the regiochemistry of adduct formation. © 2007 American Chemical Society.


Publication metadata

Author(s): Higham LJ, Muldoon J, Kelly PG, Corr DM, Muller-Bunz H, Gilheany DG

Publication type: Article

Publication status: Published

Journal: Journal of Organic Chemistry

Year: 2007

Volume: 72

Issue: 23

Pages: 8780-8785

ISSN (print): 0022-3263

ISSN (electronic): 1520-6904

Publisher: American Chemical Society

URL: http://dx.doi.org/10.1021/jo7014104

DOI: 10.1021/jo7014104

PubMed id: 17949041


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