Electron loss from 1, 3, 3-trimethyl-2-azabicyclo [2.2. 2] octane derivatives. Is. sigma.-coupling thermodynamically important?

SF Nelsen, RJ Qualy, PM Gannett

Index: Nelsen, Stephen F.; Qualy, Richard J.; Gannett, Peter M. Journal of Organic Chemistry, 1982 , vol. 47, # 25 p. 4879 - 4881

Full Text: HTML

Citation Number: 1

Abstract

Results To make the thermodynamically significant E"'measurements, we require radical cations that have long lifetimes under CV conditions (approximately 1 mM in neutral form). For most substituents on nitrogen, this requires Bredt's rule protection because the neutral form deprotonates the radical cation so rapidly. We had initially envisaged carrying out the comparison on 6 and its non-