64823-94-5

Upstream product

• 4837-31-4 4-Phenylsulfanyl-morpholine 
• 627-27-0 homoalylic alcohol 
• 5016-90-0 but-3-en-1-yl 2,2,2-trifluoroacetate 
• 882-33-7 diphenyldisulfane 
• 64168-52-1 4'-nitrobenzenesulfenanilide 
• 542-88-1 bis(2-chloromethyl)ether 
• 1822-73-7 phenylthioethylene 
• 1191-99-7 2,3-dihydro-2H-furan 
• 108-98-5 thiophenol 

Relevant academic research and scientific papers

Cyclic Ether Formation with N-(Phenylthio)morpholine

Cyclic ethers with 5- to 7-membered rings are formed by sulphenoetherification of unsaturated alcohols with N-(phenylthio)morpholine and trifluoromethanesulphonic acid.

'Tailor-made' carbonyl ylides: [3 + 2] Cycloaddition of the parent and optionally substituted nonstabilized carbonyl ylides

'Tailor-made' carbonyl ylides bearing only alkyl substituents or no substituents were efficiently generated from α-chloroalkyl α'-chloroalkyl ethers in the presence of samarium reagents. Using these novel and synthetically practical carbonyl ylides, optionally substituted and stereochemically defined tetrahydrofurans dihydrofurans and dioxolane were synthesized in a single step.

Highly selective anti-Markovnikov addition of thiols to vinyl ethers under solvent- and catalyst-free conditions

A simple and efficient protocol for the anti-Markovnikov addition of thiols to vinyl ethers under solvent- and catalyst-free conditions has been established. A series of thiol ethers containing oxygen atom were obtained with good to excellent yields.

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.

Regioselective Synthesis of Hydroxy Sulphides via Trifluoroacetoxysulphenylation of Derivatives of Allylic Alcohols

Reaction of manganese(III) acetate with diphenyl disulphide in dichloromethane-trifluoroacetic acid in the presence of allylic esters gives trifluoroacetoxy sulphides, which on hydrolysis readily afford vicinal hydroxy sulphides.With acetate esters, neighbouring group participation by the acetate functionality controls the reaction course.Thus regiospecific addition to allyl acetate affords after hydrolysis only 3-phenylthiopropane-1,2-diol.In contrast, with trifluoroacetate esters the inductive effects of the trifluoroacetate functionality lead to a different regiocontrol.Thus addition of diphenyl disulphide to allyl trifluoroacetate gives after hydrolysis only 2-phenylthiopropane-1,3-diol.The regio- and stereochemistry of addition to a variety of other allylic (and homoallylic) esters is described and the extension of this type of regiocontrol is discussed.