Vinyloxocarbenium Ions in 4 + 3 Cycloadditions. Bromination of an Alkoxyenone, Cycloaddition Chemistry of the Adduct and Chemistry of the Cycloadducts

Michael Harmata; Paitoon Rashatasakhon

doi:10.1055/s-2000-7643

Synlett 2000; 2000(10): 1419-1422
DOI: 10.1055/s-2000-7643

letter

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Vinyloxocarbenium Ions in 4 + 3 Cycloadditions. Bromination of an Alkoxyenone, Cycloaddition Chemistry of the Adduct and Chemistry of the Cycloadducts

Michael Harmata^* , Paitoon Rashatasakhon

^*Department of Chemistry, 123 Chemistry Building, University of Missouri-Columbia, Columbia, Missouri 65211, USA; E-mail: harmatam@missouri.edu

Abstract

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Treatment of 3-methoxy-3-buten-2-one with 1 equivalent of bromine results in a labile dibromo adduct. Strirring this compound and triethylamine in the presence of a diene like furan results in the stereoselective formation of a 4 + 3 cycloaddition product in good yield. Several examples of this reaction are reported as is the interesting chemistry associated with the 4 + 3 cycloadduct derived from furan.

cycloadditions - carbocations - regioselectivity - radical reactions - ring opening

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