Date of Award

12-2007

Level of Access

Campus-Only Thesis

Degree Name

Master of Science (MS)

Department

Chemistry

Advisor

Bruce Jensen

Second Committee Member

Barbara J.W. Cole

Third Committee Member

Carl P. Tripp

Abstract

The effect of a strongly electron - releasing substituent at the 6-position of 1- benzyl-2-tetralones results in regiospecific Beckmann rearrangements from the corresponding oximes. Previous data support that ortho-substituents on the 1-benzyl group display steric controls during this reaction. Data presented herein demonstrate how stereoelectronic controls offered by the methoxyl group can be used for the convenient syntheses of the 2-benzazepinones. A mechanism, supported by molecular modeling calculations, has been proposed for this process.

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