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

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

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被引用次数: 0

摘要

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 ...