On the Reaction of Thioacetals with Sulphuryl Chloride

DOI: 10.1039/P19810000457

Source and publish data:

Journal of the Chemical Society. Perkin transactions I p. 457 - 461 (1981)

Update date:2022-08-05

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Authors:

Bulman-Page, Philip C.

Ley, Steven V.

Morton, Judith A.

Williams, David J.

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Article abstract of DOI:10.1039/P19810000457

Sulphuryl chloride reacts with 1,3-oxathiolans and 1,3-dithiolans to afford unstable intermediate trans-2,3-dichloro-1,4-oxathians or trans-2,3-dichloro-1,4-dithians.Some of these intermediates can be converted on hydrolytic work up to α-ketothioacetals in reasonable yield.Intermediates in the rearrangement pathway have been identified.Reaction of 6-oxospiro (4) with toluene-p-sulphonic acid gave 2,14-dioxa-11-thiatetracyclo<7.5.3.0^1,10.0^3,8>heptadec-3-en-4-one (20), a novel tetracyclic compound whose structure was determined by X-ray crystallography.

Full text of DOI:10.1039/P19810000457

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