A Stereospecific2??Aza??divinylcyclopropane'Rearrangement

P Müller, JL Toujas, G Bernardinelli

Index: Mueller, Paul; Toujas, Jean-Louis; Bernardinelli, Gerald Helvetica Chimica Acta, 2000 , vol. 83, # 7 p. 1525 - 1534

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Citation Number: 11

Abstract

Abstract The stereochemical course of the thermal 2-aza-Cope rearrangement of the optically pure acyl azide (−)-(1S)-5 was investigated by determination of the absolute configuration of the rearrangement product (1R, 8S)-9. The reaction proceeds by a sequence of stereospecific steps from 5 to an equilibrating mixture of exo-and endo- isocyanates 6 and 7. The endo-isomer 7 undergoes Cope rearrangement to the putative ...