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Catalytic rearrangement of o cholesteryl s alkyl dithiocarbonates to s alkyl s cholesteryl dithiocarbonates by phenols



Catalytic rearrangement of o cholesteryl s alkyl dithiocarbonates to s alkyl s cholesteryl dithiocarbonates by phenols



Chemical & Pharmaceutical Bulletin 33(5): 1861-1868



Phenolysis of O-cholesteryl-S-alkyldithiocarbonates gave the corresponding S-alkyl-S-cholesteryldithiocarbonates. The arrangements obeyed first-order rate laws and the rates were affected by the acidity of the phenols. A plot of the substituent effect of the S-alkyl moiety against the Tafts .sigma.* values was roughly linear, o-Substituted phenols such as 2-chlorophenol or 2,6-dimethylphenol considerably retarded the rearrangement. The role of phenols and the reaction behavior of O-cholesteryl-S-alkyldithiocarbonates are discussed on the basis of kinetic and molecular orbital calculation data indicating that the rearrangement may proceed by specific solvation of phenols at the thiocarbonyl sulfur atom.

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Accession: 004887238

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DOI: 10.1248/cpb.33.1861


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