27694-08-2Relevant articles and documents
Efficient hydrolysis of dithioacetals by the N-fluoro-2,4,6-trimethylpyridinium triflate-water system
Kiselyov,Strekowski,Semenov
, p. 2151 - 2158 (2007/10/02)
Dithioacetals including 1,3-dithianes and 1,3-dithiolanes are efficiently cleaved by the title reagent system to the parent carbonyl compounds. The cleavage of diprotected symmetrical α-diketones and p-phenylenediketones gives monoketones in good yields. Amide, 1,3-dioxolane, disulfide, ester, ether, hydroxy, nitrile, nitro, and sulfide functions are relatively stable under the cleavage conditions but thiols are oxidized to disulfides.
The substrate- and stereoselectivity of microbial reductions of 1,4-dithiaspirodecanones and 1,5-dithiaspiroundecanones
Takemura, Tetsuo,Hosoya, Yoshiko,Mori, Nobuo
, p. 523 - 529 (2007/10/02)
The title spirocyclic ketones, possessing possible substitution patterns 1,4-dithiaspirodecan-6-one (1a), -7-one (3a), and -8-one (5a) and 1,5-dithiaspiroundecan-7-one (2a), -8-one (4a), and -9-one (6a), have been reduced with new strains of yeast (Saccharomyces cerevisiae, JCM 1819 and JCM 2214).Reductions of the prochiral ketones 1a-4a occur with high enantiofacial selectivity on the preparative scale (up to 99percent ee).The product alcohols (1,4-dithiaspirodecan-6-ol (1b) and -7-ol (3b) and 1,5-dithiaspiroundecan-7-ol (2b) and -8-ol (4b)) have theS configuration, as confirmed by 2D COSY experiments of the (S)-MTPA ester of 1b-4b using the configuration correlation model of Mosher.
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.
