Author

Ping Lu

Defense Date

12-22-2009

Graduation Date

2009

Availability

Immediate Access

Submission Type

thesis

Degree Name

MS

Department

Chemistry and Biochemistry

School

Bayer School of Natural and Environmental Sciences

Committee Chair

Fraser Fleming

Committee Member

Bruce Beaver

Committee Member

Ellen Gawalt

Keywords

Metalated, Nitrile

Abstract

Two different strategies examine intramolecular cyclizations of chiral, metalated nitriles. Cyclizations onto allylic electrophiles through competitive SN2 or SN2' displacements have different trajectories reflecting the different conformations within the forming ring. Deuterium labeling with allylic electrophiles reveals an inherent preference for SN2 displacements reflecting the optimal orbital overlap for the two different geometries.

Format

PDF

Language

English

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