Date of Award
12-2007
Level of Access Assigned by Author
Campus-Only Thesis
Degree Name
Master of Science (MS)
Department
Chemistry
First Committee 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.
Recommended Citation
Silvary, Sunil Raj, "StereoElectronic Controls in the Preparation of 1-Benzyl-l, 2, 4, 5-Tetrahydro-(3H)-2-Benzazepin-3-ones Via Beckmann Rearrangement" (2007). Electronic Theses and Dissertations. 917.
https://digitalcommons.library.umaine.edu/etd/917