27694-08-2Relevant academic research and scientific papers
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.
Preparation of Some Oxa- and Thia-decalins and -propellanes. Barriers to Conformational Interconversion
Fjeldskaar, Inger Reidun,Skatteboel, Lars
, p. 410 - 417 (2007/10/02)
Reactions of 5,6-dihydro-2,3-dimethyl-1,4-dioxin, -1,4-oxathiin and -1,4-dithiin with bromine in the presence of 1,2-ethanediol, 2-mercaptoethanol and 1,2-ethanedithiol, respectively, afforded, in most cases, high yields of the corresponding oxa- and thia-decalins as cis-isomers only.Similar reactions of the bicyclic dihydrodioxins, 2,5-dioxabicyclodec-1(6)-ene and the sulfur analogues gave the corresponding propellanes in high yields.The barriers to conformational interconversion were obtained from variable temperature NMR spectra.Other examples of propellanes were obtained; addition of dihalocarbenes to the bicyclic dihydrodioxins furnished the corresponding dihalocyclopropane derivatives, and the photochemical addition of benzophenone gave the expected oxetane.
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.
Indirekte elektro-organische Synthesen - ein modernes Kapitel der organischen Elektrochemie
Steckhan, Eberhard
, p. 681 - 699 (2007/10/02)
Die elektrochemische Erzeugung und Regeneration von Redox-Agentien fuer organische Synthesen (indirekte Elektrolyse) erweitert das Potential der Elektrochemie, da vielfach hoehere oder ganz anders geartete Selektivitaeten bei gleichzeitig deutlich erniedr
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.
