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Acyl anion equivalent with some advantages over 1,3-dithiane for the preparation of vinyl sulfides. Bis(phenylthio)methane is used in the synthesis of the dihydroxy thioethers.
Abel Mendoza.; Donald S. Matteson. Bis(phenylthio)methaneboronic esters as sources of carbanions and ketene thioacetals. J. Org. Chem. 1979, 44, (8), 1352-1354.
Francisco Foubelo.; Ana Gutierrez.; Miguel Yus. Methane-derived polyanionic synthons from bis(phenylthio)methane. Tetrahedron Letters. 1999, 40, (46), 8177-8180.
Acyl anion equivalent, compare 1,3-Dithiane, A10505. Can be metallated, e.g. with n-BuLi. Dimetallation requires a metal complexing agent, e.g. TMEDA, allowing dialkylation: Tetrahedron Lett., 21, 4763 (1980).
The products of addition of the lithio-derivative to aldehydes and ketones undergo a pinacol-type rearrangement with CuOTf, with insertion of a one-carbon unit adjacent to the carbonyl group: J. Am. Chem. Soc., 97, 4749 (1975); see also: Org. Synth. Coll., 6, 737 (1988). An alternative method utilizes an alkyllithium to effect a carbenoid rearrangement, which has been applied to ring expansion: Tetrahedron Lett., 28, 20 (1987):