Cytotoxic compounds. Part XIII. Some 1-arylthiopropan-2-ols and 2-arylthiopropanols. Rearrangement of the primary methanesulphonates into the secondary isomers
Abstract
Syntheses of the title alcohols are described, where the aryl group is phenyl, p-chloro-, p-methoxy-, p-methylthio-, 2,4-dinitro-phenyl, and 2-naphthyl; also the acetates and methyl ethers of all except the naphthyl compounds. Except for the 2,4-dinitrophenyl derivative (prepared in the normal way with methanesulphonyl chloride) the secondary methanesulphonates could only be obtained by the use of methanesulphonic anhydride under special conditions. Of the primary alcohols, the 2,4-dinitrophenyl compound gave the primary methanesulphonate but all the others gave mainly the secondary methanesulphonates.
The rates of solvolysis of the secondary methanesulphonates in methanol, and the 1H n.m.r. spectra of the alcohols and of their derivatives, are tabulated.
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