A Phenyliodonium Ylide as a Precursor for Dicarboethoxycarbene: Demonstration of a Strategy for Carbene Generation
Document Type
Article
Department or Administrative Unit
Chemistry
Publication Date
5-10-2000
Abstract
Thermal or photochemical decomposition of carbene precursors, especially diazocompounds and diazirenes, leads in many cases to both a free carbene intermediate and products formed directly from the precursor. This ability of precursors to mimic carbenes often complicates mechanistic studies. For example,direct photolysis of dimethyl diazomalonate leads to products stemming from reactions of substrate with1:C(CO2Me)2,3:C(CO2-Me)2, and photoexcited1a(11a*) as outlined in Scheme 1. In situations such as this, alternative modes of carbene generation have proved valuable in characterizing the reactive species. Here we describe a strategy for identifying new carbene precursors and report the facile generation of 1:C(CO2Et)2by thermal decomposition of iodonium ylide, as well as a supporting computational study.
Recommended Citation
Camacho, M. B., Clark, A. E., Liebrecht, T. A., & DeLuca, J. A. P. (2000). A Phenyliodonium Ylide as a Precursor for Dicarboethoxycarbene: Demonstration of a Strategy for Carbene Generation. Journal of the American Chemical Society, 122(21), 5210–5211. https://doi.org/10.1021/ja000334o
Journal
Journal of the American Chemical Society
Rights
Copyright © 2000 American Chemical Society
Comments
This article was originally published in Journal of the American Chemical Society. The full-text article from the publisher can be found here.
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