. alpha.-Disulfoxide formation during the m-chloroperoxybenzoic acid oxidation of S-(2, 2-dimethylpropyl) 2, 2-dimethylpropanethiosulfinate

F Freeman, CN Angeletakis

Index: Freeman,F.; Angletakis,C.N. Journal of the American Chemical Society, 1982 , vol. 104, p. 5766

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Citation Number: 32

Abstract

Abstract: Diastereomeric a-disulfoxides (14) have been detected as intermediates in the m- chloroproxybenzoic acid (MCPBA) oxidation of neopentyl neopentanethiosulfinate (6) at-40 OC in CDC13 via'H NMR and I3C NMR spectroscopy. The product mixture at-40 OC contained 6, 14, neopentyl neopentanethiosulfonate (7), and neopentanesulfinic acid (11). Oxidation of 6 at-20 OC, followed by warming to 0 OC and treatment with NaHC03, gave ( ...