Date of Award
12-2007
Level of Access Assigned by Author
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.
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