127901-02-4

Upstream product

• 76200-34-5 1-(phenylthio)-1-(trimethylsilyl)propane 
• 123289-30-5 1-(Phenylthio)-1-(trimethylsilyl)-1,2-propadiene 
• 108-94-1 cyclohexanone 
• 100-52-7 benzaldehyde 
• 123-72-8 butyraldehyde 
• 6212-77-7 1-phenylthio-1-propyne 
• 882-33-7 diphenyldisulfane 
• 1066-54-2 trimethylsilylacetylene 
• 98-86-2 acetophenone 

Relevant academic research and scientific papers

Reaction of Diphenyl Disulfide with Alkynes Promoted by Di-tert-butyl and Dibenzoyl Peroxides: a Useful Syntheic Route to 3- (and 2,3) Substituted Benzothiophenes

Thermal reactions of diphenyl disulfide 1 with phenylacetylenes 2a-e promoted by di-tert-butyl peroxide (TBP) at 110 or 150 deg C provides a useful synthetic route to the (2-substituted) 3-phenylbenzothiophenes 4a-e, which result from intramolecular cyclization of 1-phenyl-2-(phenylthio)vinyl radical intermediates 3a-e.Similar reactions of the disulfide 1 with tert-butyl- and trimethylsilylacetylenes 2f and 2g also provide the corresponding benzothiophenes 4f and 4g in satisfactory yields; low yields of the benzothiophene products 4h, i, however, are obtained with hex-1-yne 1h and hex-3-yne 1i.Evidence is presented that the thermal reaction of the disulfide 1 with the alkynes 2 at 100 deg C in the presence of dibenzoyl peroxide, while being of little use for the synthesis of benzothiophenes 4, generally leads to the 2-(phenylthio)vinyl benzoates 10; this is ascribed to initial addition of benzoyloxy radicals to alkyne triple bonds.

Hydroalumination and related reactions of phenyl 1-(trimethylsilyl)propadienyl sulfide followed by quenching with carbonyl compounds

Phenyl 1-(trimethylsilyl)propadienyl sulfide undergoes a hydroalumination with diisobutylaluminum hydride (DIBAH) or lithium butyl(diisobutyl)aluminum hydride (BL-DIBAH). The adduct anion derived from DIBAH is regioselectively trapped with carbonyl compounds at the position α to the phenylthio moiety to give 1,3-dienes as Peterson olefination products; the anion derived from BL-DIBAH is trapped at the position γ to the phenylthio moiety to give 3-buten-1-ols. Silylmetalation and stanylalumination on the same acceptor have been also briefly investigated as equivalent reactions.

A Facile Stereoselective Synthesis of α-Silyl Substituted Vinyl Sulfides

A facile one-pot synthesis of α-silyl substituted vinyl sulfides which involves the chlorination of 1-phenylthio-1-silylalkanes followed by dehydrochlorination is described.