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Optically active 2,3-epoxy sulfides as precursors to 3-hydroxy-1,2-dithioethers and 3-hydroxy-1-alkenylthioethers

✍ Scribed by Ian Forristal; Kevin R. Lawson; Christopher M. Rayner

Book ID: 104262209
Publisher: Elsevier Science
Year: 1999
Tongue: French
Weight: 250 KB
Volume: 40
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(99)01427-6

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✦ Synopsis

Procedures are reported for the conversion of 2,3-epoxysulfides to 3-hydroxy-1,2-dithioethers. Conventional nucleophih'c ring opening using a thiolate gives a mixture of products resulting from ring opening at C-2 and C-3, with the latter predominating. With sodium thiolates in DMF a competing [5-elimination process is observed to form 3hydroxy-1-alkenylthioethers. Alternatively, Lewis acid induced thiiranium ion generation from a 2,3-epoxy sulfide, and nucleophilic ring opening with S-trimethylsilylthiophenol gives 3-hydroxy-1,2-dithioethers with full regio-and stereo-control.

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