6178-57-0

Upstream product

• 592-41-6 1-hexene 
• 64168-52-1 4'-nitrobenzenesulfenanilide 
• 110-62-3 pentanal 
• 17873-08-4 (phenylsulfanylmethyl)trimethylsilane 
• 1436-34-6 1,2-Epoxyhexane 
• 108-98-5 thiophenol 

Relevant academic research and scientific papers

Addition of unactivated thiols to epoxides and oxetanes catalyzed by a rhenium-oxo complex

A method for synthesizing β- and γ-hydroxy thioethers via addition of unactivated thiols to epoxides and oxetanes has been developed. This reaction is proposed to proceed through an unconventional mode of activation of the heterocycles. The transformation is catalyzed by ReO2I(PPh 3)2 affording β- and γ-hydroxy thioethers in moderate to excellent yield with excellent regioselectivity.

Efficient ring-opening reaction of epoxides and aziridines promoted by tributylphosphine in water

Tributylphosphine was found to be an effective promoting reagent for the ring-opening reaction of various epoxides and aziridines with nucleophile to produce corresponding anti-bifunctional products in moderate to excellent yields in water.

Reaction of 4′-nitrobenzenesulfenanilide (NBSA) with Lewis acids. A study of its application in sulfenocyclization of alkenes and alkynes

Phenylsulfenocyclization of a number of alkenes and alkynes possessing internal hydroxyl, carboxyl or vinyl functionality has been investigated with NBSA. Thioetherification of 4-penten-1-ol 4 as well as thiolactonization of 4-penten-1-oic acid 7 and, to a modest extent, 4-pentyn-1-oic acid 8 can be successfully achieved with NBSA in the presence of boron trifluoride. On the other hand, under analogous conditions 3-buten-1-ol 3 and 3-buten-1-oic acid 6 fail to undergo thiocyclization and give instead oxa- and/or aza-sulfenylation 1,2-adducts. Similar failure is observed with 4-pentyn-1-ol 5, in which case diphenyl disulfide and 4-nitroaniline are the exclusive products. Hexa-1,5-diene 9, to some extent, affords a cyclized arylaminosulfide, i.e. 23, ascribable to formal loss of a methylene unit from the initial (phenylthiomethyl)- cyclopentyl cation 24. The reaction products are discussed in terms of intermediate thiiranium and thiirenium ions whose decomposition mode is strictly dependent upon their structural features. Novel evidence is also presented that aluminium chloride and bromide can promote reaction of NBSA with alkenes and alkynes to afford chloro- and bromo-sulfenylation adducts in varying yields.

NOVEL ARYLTHIOMETHYLATION OF CARBONYL COMPOUNDS USING ARYLTHIOMETHYLTRIMETHYLSILANES CATALYZED BY FLUORIDE IONS. NEW ROUTE TO β-HYDROXYARYLSULFIDES

Arylthiomethyltrimethylsilanes are good and mild nucleophilic reagents for introducing arylthiomethyl groups into carbonyl compounds promoted by tetra-n-butylammonium fluoride to give the corresponding β-hydroxyarylsulfides in fairly good yields.

BORON TRIFLUORIDE PROMOTED REACTION OF BENZENESULPHENANILIDES WITH ALKENES

The boron trifluoride-promoted reaction of a series of 3'- and 4'-substituted benzenesulphenanilides (1) with various alkenes has been investigated as a potential synthetic route to arylaminosulphides.The benzenesulphenanilides (1) investigated generally afford arylaminosulphenylation adducts in fair to good yields except for the methoxy-substituted anilides (1e and f), which largely lead to decomposition products under comparable conditions.In all cases examined, the addition proceeds with trans-stereospecificity and, with terminal alkenes, leads regioselectively to the exclusive (or predominant) formation of the terminal sulphides.The findings are interpreted by assuming that boron trifluoride transforms the sluggish benzenesulphenanilides (1) into reactive electrophilic species, which can undergo nucleophilic attack at sulphur by an alkene, presumably affording episulphonium-borate ion-pair intermediates, in competition with attack by another sulphenanilide unit.