Alkylation of aldehyde arenesulfonylhydrazones via trialkylboranes

Author

John Thortan Maddox

Date of Award

8-1995

Degree Type

Dissertation

Degree Name

Doctor of Philosophy

Major

Chemistry

Major Professor

George W. Kabalka

Committee Members

David C. Baker, John Feller

Abstract

A new methodology for delivering alkyl groups to carbonyl moieties via trialkylboranes was developed. This new reaction is a useful alternative to the traditional alkylmetal reactions.

Arenesulfonylhydrazone derivatives of aryl aldehydes are easily alkylated by trialkylboranes in the presence of base to give the corresponding substituted alcohols after oxidation. Both tosyl and trisyl derivatives may be utilized in this new reaction. The reaction tolerates several different functional groups thereby allowing functionalized alkyl groups to be transferred. The applicability of various blocked borane derivatives was also evaluated.

The methodology can be extended to alkyl aldehydes via the trisyl derivatives. The usefulness of blocked borane derivatives was evaluated.

Several approaches to the direct 1,2-addition of a trialkylborane to a carbonyl group were attempted. Future approaches to this problem were also discussed.

Recommended Citation

Maddox, John Thortan, "Alkylation of aldehyde arenesulfonylhydrazones via trialkylboranes. " PhD diss., University of Tennessee, 1995.
https://trace.tennessee.edu/utk_graddiss/10043