Synthesis of Polyfunctional Organosulfur Compounds Mediated by Azetidinium­ Salts

Abstract

Ring-opening of N,N-dialkyl-3-hydroxyazetidinium chlorides 1a-d with sulfur nucleophiles leads to C-S bond formation furnishing polyfunctional sulfides, sulfonates and thiosulfonates.

Key words

alkylation - heterocycles - nucleophiles - ring opening - sulfonates

References

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10

For example: 4b = MOPSO sodium salt: Fluka 69941, Sigma M5914.

18

The higher than commonly acceptable differences between calculated and found data of some elemental analyses for compounds 2 and 4 can arise from contamination with NaCl which is hard to remove by crystallization. The purified salt 2d (column chromatography) may contain trace amounts of the free acid 6d.