β-KETOSULFINYL CHLORIDES AND RELATED COMPOUNDS

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Abstract
Isopropyl β-ketosulfinyl chlorides may be prepared in high yields by treating the appropriate isopropyl ketone with thionyl chloride under mild conditions. β-Ketosulfinyl chlorides do not appear to have been previously reported in the literature. Analytical and spectral data indicate that in cases where α and α' protons are adjacent to the carbonyl group only the α-proton of the isopropyl group is substituted giving a monosulfinyl chloride. In certain cases where the α'-proton is activated cyclization and reduction may occur to give the substituted thietan-3-one. Comparable chloro-compounds have been prepared by treating the ketone with sulfuryl chloride. Anomalous nmr spectra obtained for certain compounds have been further studied using variable temperature techniques and various solvents. An attempt was made to prepare the β-ketosulfinamides, and the compounds obtained were found to be unstable.

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