PhSH

PhSH, BF3-Et20, CHCI3, 0°, 10 min, 86% yield. ZnCl2 and MgBr2 have also been used as catalysts. With MgBr2 acetals can be converted to thioketals in the presence of ketones. ... 

From a dialkyl acetal MgBr2, Et20, it, PhSH, 91% yield. MOM groups are converted to phenylthiomethyl groups, 75% yield. 

PhSH. This reagent affords the phenyl disulfide. ... 

PhSH, >50° or HSCH2CO2H, 45°, 15 h, quant. The 5-ethyl disulfide is stable to acid-catalyzed hydrolysis (CF3CO2H) of carbamates and to am-monolysis (25% NH3/CH3OH).-... 

CF3COOH, PhSH, 20°, 1 h, 100% yield. Thiophenol is used to scavenge... 

Me2BBr, TEA, BH3-THF, —78° warm to —20° over 1 h, 70-97% yield. These conditions cleave the benzylidene acetal, to leave the least hindered alcohol as a free hydroxyl. If diborane is omitted from the reaction mixture and the reaction is quenched with PhSH and TEA, the benzylidene group is cleaved to give an (9,5 -acetal [ROCH(SPh)Ph]. Acetonides are cleaved similarly." ... 

CS2CO3, PhSH, DMF, 85°, 3 h, 91% yield. A methyl carbonate was cleaved simultaneously. 

The o-nitrobenzenesulfenamide has been used for the protection of amino acids. o-Nitrobenzenesulfenamides, B, are also cleaved by acidic hydrolysis (HCl/Et20 or EtOH, 0°, 1 h, 95% yield)" by nucleophiles (13 reagents, 5 min-12 h, 90% cleaved) by PhSH or HSCH2CO2H, 22°, 1 h by 2-mercaptopyri-dine/CH2Cl2, 1 min, 100% yield) by NH4SCN, 2-methyl-1-indolylacetic acid and by catalytic desulfurization (Raney Ni/DMF, column, a few hours, satisfactory yield). 

K2CO3 or CS2CO3, DMF or CH3CN, PhSH, 88-96% yield. This process is not always selective for p-nosylate cleavage. Some amines, especially cyclic ones, tend to form 4-phenyl thioethers by nitro displacement as by-products of the cleavage process. This seems to be true only for the p-nosylate. ... 

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