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Cycloaddition reactions

Communication 1. Reaction of sulfenes with α,β-unsaturated sulfides

  • Organic and Biological Chemistry
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Bulletin of the Academy of Sciences of the USSR, Division of chemical science Aims and scope

Conclusions

The reactions ofα, β-unsaturated sulfides with sulfenes are quite dependent on the nucleophilicity of the multiple bond of the vinyl sulfide, and on the electrophilicity of the sulfene, and lead to the formation of dioxythietanes, containing various functional groups, in 30–70% yields.

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Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 8, pp. 1827–1831, August, 1974.

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Prilezhaeva, E.N., Petukhova, N.P., Kurilkin, V.I. et al. Cycloaddition reactions. Russ Chem Bull 23, 1745–1748 (1974). https://doi.org/10.1007/BF00923202

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  • DOI: https://doi.org/10.1007/BF00923202

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