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Issue 9, 2014
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The conversion of allenes to strained three-membered heterocycles

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Abstract

This article reviews methods for converting allenes to strained, three-membered methylene heterocycles, and also covers the reactivity of these products. Specifically, the synthesis and reactivity of methylene aziridines, allene oxides/spirodiepoxides, methylene silacyclopropanes, methylene phosphiranes, and methylene thiiranes are described, including applications to the synthesis of complex molecules. Due to the primary focus on heterocyclic motifs, the all-carbon analogue of these species (methylene cyclopropane) is only briefly discussed.

Graphical abstract: The conversion of allenes to strained three-membered heterocycles

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Article information


Submitted
15 Nov 2013
First published
20 Mar 2014

Chem. Soc. Rev., 2014,43, 3136-3163
Article type
Review Article
Author version available

The conversion of allenes to strained three-membered heterocycles

C. S. Adams, C. D. Weatherly, E. G. Burke and J. M. Schomaker, Chem. Soc. Rev., 2014, 43, 3136
DOI: 10.1039/C3CS60416K

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