The Journal of Organic Chemistry

Study of reactions leading to sulfine formation. Competition of reaction pathways in the reaction of methoxide ion with methyl 1-naphthylmethanesulfinates

JL Kice, H Lotey

Index: Kice, John L.; Lotey, Harvinder Journal of Organic Chemistry, 1989 , vol. 54, # 15 p. 3596 - 3602

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Citation Number: 5

Abstract

In CD30-/CD30D methyl 1-naphthylmethanesuhates, NpCH2S (0) OCH3 (2), undergo both exchange of CH30 by CD30 by substitution at the sulfinyl group and elimination to form the sulfine, NpCH= S= O. With use of methyl (2-methoxy-1-naphthy1) methanesulfinate (2a) it has been shown that formation of the sulfine takes place by an (ElcB) i, mechanism. The rates of substitution (k3 and elimination (kJ of a series of 2 have been determined in CD30 ...