Bredt's rule kinetically stabilized nitrogen-centered radical cations and radicals in the 9-azabicyclo [3.3. 1] nonyl system

SF Nelsen, CR Kessel, DJ Brien

Index: Nelsen, Stephen F.; Kessel, Carl R.; Brien, David J. Journal of the American Chemical Society, 1980 , vol. 102, # 2 p. 702 - 711

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Citation Number: 64

Abstract

Abstract: Derivatives of 9-azabicyclo [3.3. l] nonane (9-ABN) where the substituent at N9 is CR3, NR2, OR, CI, NMe3+, and carbonyl, and of doubly bonded immonium salts (9-ABN= Y)+, where Y= CRR', NR', and 0, were studied, along with 9-ABN-substituted p- phenylenediamine, 2-tetrazene, and 4-tert-butylaniline. 9-tert-Butyl-9-ABN is argued to be strongly pyramidal at N9, and a methodology for estimating pyramidality at nitrogen of ...