The Journal of organic chemistry

Synthesis of Bridgehead Nitrogen Heterocycles via Cyclization of α-Ammonio 5-Hexenyl Radicals

EW Della, PA Smith

Index: Della, Ernest W.; Smith, Paul A. Journal of Organic Chemistry, 1999 , vol. 64, # 6 p. 1798 - 1806

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Citation Number: 24

Abstract

Ring-closure of the 2, 2-dimethyl-2-azonia-5-hexenyl radical (4) proceeds smoothly and efficiently to give the 5-exo isomer essentially quantitatively, in accordance with predictions based on MP4SDTQ/6-31G* ab initio calculations on the thermodynamic stability of α- ammonio radicals. The corresponding 5-hexynyl radical species 15 and its 6-phenyl derivative 19 display similar behavior affording the analogous 5-exo-3- ...