Chemo-and Diastereoselectivity in the Dimethyldioxirane Oxidation of 2, 3-Dihydro-4 H-1-benzothiopyran-4-ones and 4 H-1-Benzothiopyran-4-ones. Unusual …

…, P Kövér, M Németh, EM Peters, K Peters

Index: Patonay; Adam; Levai; Koever; Nemeth; Peters Journal of Organic Chemistry, 2001 , vol. 66, # 7 p. 2275 - 2280

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Citation Number: 30

Abstract

The oxidation of the 1-thiochromanones 1-3 by dimethyldioxirane (DMD) produced the corresponding sulfoxides 4-6 or sulfones 7-9; their relative amounts depended on the amount of oxidant used. A low diastereoselectivity was observed in the sulfoxidation of the 2- substituted 1-thiochromanones 2 and 3, due to the small steric differentiation during the DMD attack. An unusual reactivity pattern was found in the DMD oxidation of the 1- ...