33266-05-6Relevant articles and documents
Studies of π-diastereofacial selectivity: The influence of α- oxathiolane ketals on cyclic ketones
Dimitroff, Martin,Fallis, Alex G.
, p. 2527 - 2530 (1998)
The facial influence and synthetic utility of oxygen and sulfur heteroatoms adjacent to carbocyclic ketones upon nucleophilic addition has been investigated. Addition to the carbonyl group displayed a preference for attack anti to sulfur and syn to oxygen in synthetically useful ratios. Diisopropylaluminum hydride reduction in the cyclopentanone series reversed this facial preference.
On the Reaction of Thioacetals with Sulphuryl Chloride
Bulman-Page, Philip C.,Ley, Steven V.,Morton, Judith A.,Williams, David J.
, p. 457 - 461 (2007/10/02)
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-thiatetracyclo1,10.03,8>heptadec-3-en-4-one (20), a novel tetracyclic compound whose structure was determined by X-ray crystallography.
