3, 5, 7-Trimethyl-1-azatricyclo [3.3. 1.13, 7] decan-2-ylidene, an Aminocarbene without π Conjugation

…, IV Komarov, AJ Kirby, M Jones

Index: Ye, Qing; Komarov, Igor V.; Kirby, Anthony J.; Jones Jr., Maitland Journal of Organic Chemistry, 2002 , vol. 67, # 26 p. 9288 - 9294

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Citation Number: 18

Abstract

3, 5, 7-Trimethyl-1-azatricyclo [3.3. 1.13, 7] decan-2-ylidene, an aminocarbene without π conjugation, has been generated from the corresponding tosylhydrazone salt. Addition of the carbene to alkenes is stereospecifically cis, thus showing that the reacting state is singlet. Competition studies reveal that the carbene is somewhat nucleophilic, implying a measure of overlap between the lone pair on nitrogen and the empty orbital on carbon. In ...