Enhanced α-CH Acidity and Reactivity of Lewis Acid-Base Complexes in the Gas Phase

Authors

Jianhua Ren, University of the PacificFollow
Derek B. Workman, Purdue University
Robert R. Squires, Purdue University

Document Type

Article

Publication Title

Angewandte Chemie International Edition

Department

Chemistry

ISSN

1433-7851

Volume

36

Issue

20

DOI

10.1002/anie.199722301

First Page

2230

Last Page

2232

Publication Date

11-3-1997

Abstract

Borane complexation at the heteroatom increases the gas‐phase C-H acidities of dimethyl sulfide, trimethylamine, and trimethylphosphane by up to 20 kcal mol⁻¹. Deprotonation of the volatile Lewis acid–base complexes in the gas phase produces dipole‐stabilized carbanions that do not rearrange to the more stable borate isomers. The complexation also enhances the reactivity of pendant methyl and ethyl groups toward substitution and elimination reactions.

Recommended Citation

Ren, J., Workman, D. B., & Squires, R. R. (1997). Enhanced α-CH Acidity and Reactivity of Lewis Acid-Base Complexes in the Gas Phase. Angewandte Chemie International Edition, 36(20), 2230–2232. DOI: 10.1002/anie.199722301
https://scholarlycommons.pacific.edu/cop-facarticles/660