The Journal of Organic Chemistry

Exploratory Studies on Reactions of Cobaloxime π-Cations with C-Nucleophiles: Irreversible Alkene Decomplexation versus Nucleophilic Capture

JL Gage, BP Branchaud

Index: Gage, Jennifer L.; Branchaud, Bruce P. Journal of Organic Chemistry, 1996 , vol. 61, # 3 p. 831 - 837

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Citation Number: 22

Abstract

(β-Hydroxyalkyl)-and (β-acetoxyalkyl) cobaloximes can undergo facile acid-catalyzed β- heteroatom exchange with oxygen and nitrogen nucleophiles in an SN1-like mechanism via cationic metal-alkene π-complex intermediates (cobaloxime π-cations). The reaction of cobaloxime π-cations with carbon nucleophiles has not been previously reported. The results reported in this paper demonstrate that cobaloxime π-cations are reasonably good ...