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Updated: May 29, 2026

Preparation and Use of Carbonyl-decorated Carbenes in the Activation of White Phosphorus
Published on: October 3, 2014
One-pot (1-ethoxycarbonylcyclopropyl)triphenylphosphonium tetrafluoroborate ring-opening and Wittig reaction
Seung Won Chung1, Mark S Plummer, Laura A McAllister
1Antibacterial Chemistry, Worldwide Research & Development, Pfizer, Inc., Eastern Point Road, Groton, Connecticut 06340, USA. seungwon.chung@pfizer.com
Abstract:
An efficient method was developed for the synthesis of 2-methylene-4-substituted ethyl butyrates via cyclopropyl opening followed by a Wittig reaction. The desired products were formed in a two-step, one-pot reaction sequence. Alternatively, the key intermediate ylide 2 was isolable and could be stored under oxygen-free conditions and subsequently utilized. A variety of nucleophiles were found to open the commercially available cyclopropane 1. The resulting ylide reacted with aldehydes to provide E-olefinic products.
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