Reaction of tris(methylthio)methyl-lithium, tris(phenylthio)methyl-lithium, and 2-lithio-2-(methylthio)-1,3-dithiane with δ-valerolactone gives, respectively, 2-[bis(methylthio)methyl]tetrahydropyran-2-ol, phenyl tetrahydro-2-oxopyran-3-thiocarboxylate, and both 2-[2-(1,3-dithianyl)tetrahydropyran]-2-ol and 2-[2-(1,3-dithianyl)]tetrahydro-2-(methylthio)pyran-2-ol.
P. Yates, J. J. Krepinsky and A. Seif-el-nasr, J. Chem. Soc., Chem. Commun., 1989, 177 DOI: 10.1039/C39890000177
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