¹³C N.M.R. spectra of pyrrolidines and piperidines. Structure of the Perhydroisoindol-5-ones and 3-Azabicyclo[3,3,1]nonan-6-imines formed by the cyanoisopropyl radical induced cyclization of N-Methyl-N,N-bis(2-alkylallyl)amines

Abstract

The ¹³C N.M.R. chemical shifts of a series of substituted pyrrolidines and piperidines are documented and substituent parameters determined. These data have been used to assign structures to the polymers and bicyclic products formed in the cyanoisopropyl radical induced cyclizations of a series of N-methyl-N,N-bis(2-a1kylallyl)amines. The formation of perhydroisoindol-5-one and/or 3-azabi- cyclo[3,3,1]nonan-6-imine depends upon the bulk of the 2-alkyl substituent and correlates with the presence of pyrrolidine and/or piperidine units in the polymer structure.