Carbenoid insertion into the peroxide bond vs the olefin bond of cyclic peroxides

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2010

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Zvarec, O.
Avery, T.
Taylor, D.

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Journal article

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Journal of Organic Chemistry, 2010; 75(2):450-454

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Ondrej Zvarec, Thomas D. Avery and Dennis K. Taylor

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Abstract

Herein we report examples of the insertion of a carbenoid into a peroxide linkage. This study reveals that intramolecular insertion of carbenes into the peroxide linkage of 3,6-dihydro-1,2-dioxines is preferred over olefin insertion. The initial scope of the reaction and mechanistic considerations, have been probed. This methodology also generates unusual bicyclic hemiacetals (2) and tricyclic peroxides (3).

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Copyright © 2009 American Chemical Society

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