Elemental fluorine. Part 5. Reactions of 1, 3-dithiolanes and thioglycosides with fluorine–iodine mixtures

RD Chambers, G Sandford, ME Sparrowhawk…

Index: Chambers, Richard D.; Sandford, Graham; Sparrowhawk, Matthew E.; Atherton, Malcolm J. Journal of the Chemical Society - Perkin Transactions 1, 1996 , # 16 p. 1941 - 1944

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Abstract

1, 3-Dithiolanes, prepared from diaryl ketones, react with elemental fluorine–iodine mixtures to give the corresponding difluoromethylene derivatives. Under the same conditions, thioglycosides give glycosyl fluorides in good yields. Reaction of 1, 3-dithiolanes with fluorine in aqueous acetonitrile provides a remarkably mild method for efficient deprotection to the parent ketone.

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