Abstract and subjects
The 1,3-dithiane is a protected formaldehyde anion equivalent that could serve as a useful labeled synthon. We report a facile synthesis of 1,3-[2-C-13]- and 1,3-[2-C-13, 2-H-2(2)] dithiane in two steps from [C-13]-or [C-13, H-2(3)] methyl phenyl sulfoxide. We have previously reported the high yield synthesis of [C-13]methyl phenyl sulfide from [C-13]MEOH and the oxidation of [C-13]methyl phenyl sulfide to [C-13]methyl phenyl sulfoxide. Here, we describe the facile exchange of deuterium from (H2O)-H-2 into [C-13]methyl phenyl sulfoxide to yield [C-13, H-2(3)]methyl phenyl sulfoxide. Thus, from [C-13]MEOH and (H2O)-H-2, all possible C2 stable isotopomers of 1,3-dithiane are available. Our synthetic route is also amenable to preparation of radiolabeled 1,3-dithianes.