Abstract
Abstract β-Keto sulfoxides were prepared by the reaction of the esters with the methylsulfinyl carbanion. The nitrosation of the β-keto sulfoxides, RCOCH2SOCH3 (R=C6H5, C6H5CH2CH2, n-C3H7), with sodium nitrite and hydrochloric acid gave the corresponding α-chloro-α-isonitroso ketones, RCOC(=NOH)Cl, in high yields. However, the nitrosation of α-substituted β-keto sulfoxide, RCOCH(R′)SOCH3, in a similar manner afforded the α-isonitroso ketones, RCOC(=NOH)R′. The mechanisms of these reactions were studied.
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