The utilization of bridgehead intermediates in organic synthesis

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1991
Authors
Hansen, Jeffrey
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George A. Kraus
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Chemistry
Abstract

Bridgehead intermediates have only recently been employed in organic synthesis. This study was undertaken to further explore and broaden their usefulness. Reaction of 9-oxabicyclo(3.3.1) octane mesylates with Lewis acids gave bridgehead oxonium ions which could be reacted with substituted benzenes. Bridgehead sulfoxides were reacted under a variety of conditions to provide bridgehead intermediates. Thermal conditions gave a bridgehead enone that underwent an interesting rearrangement. Reaction with trifluoroacetic anhydride provided the first example of a bridgehead Pummerer reaction. Base promoted elimination afforded a bridgehead enone which was trapped by ammonia.

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Tue Jan 01 00:00:00 UTC 1991