Se-Phenyl Prop-2-eneselenoate: An Ethylene Equivalent for Diels–Alder Reactions

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Errata

This article is corrected by:

  1. Errata: Corrigendum: Se-Phenyl Prop-2-eneselenoate: An Ethylene Equivalent for Diels–Alder Reactions Volume 52, Issue 46, 11963, Article first published online: 8 November 2013

  • The mass spectrometer used in this project was supported by the National Center for Research Resources under grant number S10RR025631. The content is solely the responsibility of the authors and does not necessarily represent the official views of the National Center for Research Resources or the National Institutes of Health. The NMR spectrometers were supported by the National Science Foundation under equipment grant no. CHE-1048804.

Abstract

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Reactive: Se-phenyl prop-2-eneselenoate (phenyl selenoacrylate) 2, readily prepared from acryloyl chloride, is a very reactive dienophile in Diels–Alder reactions, and more reactive than acrylates. Its cycloadducts 3 with many dienes 1 can be easily reduced to the hydrocarbons 4 under radical conditions. This process works even in cases where there is an adjacent group that can be easily eliminated, e.g., an allylic ether.

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