The Journal of Organic Chemistry

Elimination-addition reactions of 3-[2-(arylthio) ethyl] sydnones. Displacement of the sulfide by an ether group

JN Pirl, CL Bell, L Bauer

Index: Pirl, Joerg N.; Bell, Charles L.; Bauer, Ludwig Journal of Organic Chemistry, 1982 , vol. 47, # 20 p. 3971 - 3974

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Abstract

We interpret these spectral changes in the following way. The disappearance of the triplet at 4.46 ppm is due to an HD exchange of weakly acidic active methylene protons (1-2, Scheme I). Then, in this CD30D/CD30Na solution, the sulfide is displaced by an OCD3 group to generate 6, presumably via elimination-addition reactions. Since no N-vinylsydnone (5) was detected (on the NMR time scale), it is postulated that a relatively slow p-elimination of ...

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