The silver ion induced rearrangement of n-chloro-octahydropyrindines : a sythesis of monomorine I

Author

Kenneth A. Cole

Date of Award

5-1990

Degree Type

Dissertation

Degree Name

Doctor of Philosophy

Major

Chemistry

Major Professor

Fred M. Schell

Committee Members

Ronald M. Magid, James Q. Chambers, Hildegard M. Schuller

Abstract

The effect of treating N-chloro-octahydro-1-pyrindines with silver tetrafluoroborate and subsequent hydride or trapping of the imminium ion intermediate results in good yields of indolizidines. The rearrangement of N-chloro-octahydro-1-pyrindine to indolizidine seems independent of a cis or trans fussion of the pyrindine rings and occurs with preference over alkyl substituent migration in the C-2 substituted case. Efficient trapping with cyanide and utilization of the chemistry this functionality provides led to a synthesis of monorine I.

Recommended Citation

Cole, Kenneth A., "The silver ion induced rearrangement of n-chloro-octahydropyrindines : a sythesis of monomorine I. " PhD diss., University of Tennessee, 1990.
https://trace.tennessee.edu/utk_graddiss/11283