AZABRENDANES .1. SYNTHESIS, STRUCTURE AND SPECTRAL PARAMETERS OF )-EXO-2-HYDROXY-4-AZATRICYCLO[4.2.1.0(3,7)]NONANES

A number of lfonyl)bicyclo[2.2.1]hept-2-en-endo-5-methylamines have be en synthesized from bicyclo[2.2.1]hept-2-en-endo-5-carbonitrile via re duction of the latter by lithium aluminum hydride and subsequent react ions of the resulting amine with arylsufonyl chlorides. The structures and stereochemical homogeneity of the products have been supported by the analysis of H-1 NMR spectra and by COSY-experiments. The reaction s of the sulfonamides with peroxyphthalic acid are accompanied by intr amolecular cyclizations and are completed by the formation of -exo-2-h ydroxy-4-azatricyclo[4.2.1.0(3,7)]nonanes. The structures of the subst ituted azabrendanes have been confirmed by spectral methods. The molec ular structure of l)-exo-2-hydroxy-4-azatricyclo[4.2.1.0(3,7)]nonane 8 j has been determined by X-ray diffraction analysis. (C) 1997 John Wil ey & Sons, Inc.