α,β-Unsaturated Thiocarbonyl S-Sulfides (Thiosulfines). Their Generation, Intramolecular Trapping by a Non-activated C=C Dipolarophile via Cycloaddition and trans-Sulfurization Ability

DOI: 10.1039/c39920000411

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Journal of the Chemical Society. Chemical communications p. 411 - 413 (1992)

Update date:2022-07-29

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Authors:

Saito, Takao

Nagashima, Masumi

Karakasa, Takayuki

Motoki, Shinichi

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Article abstract of DOI:10.1039/c39920000411

α,β-Unsaturated thiocarbonyl S-sulfides (thiosulfines) 10 were generated by sulfurization of the thioketones 5 and were intramolecularly trapped as 1,5-dipoles giving 8, whereas, in the presence of Et3N, they were transformed by trans-sulfurization via 1,5 cyclization into the thioketones 13 capable of undergoing the intramolecular hetero-Diels-Alder reaction to give cycloadducts 9.

Full text of DOI:10.1039/c39920000411

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