The Nitrosation of β-Keto Sulfoxides
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概要
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β-Keto sulfoxides were prepared by the reaction of the esters with the methylsulfinyl carbanion. The nitrosation of the β-keto sulfoxides, RCOCH<SUB>2</SUB>SOCH<SUB>3</SUB> (R=C<SUB>6</SUB>H<SUB>5</SUB>, C<SUB>6</SUB>H<SUB>5</SUB>CH<SUB>2</SUB>CH<SUB>2</SUB>, <I>n</I>-C<SUB>3</SUB>H<SUB>7</SUB>), 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′)SOCH<SUB>3</SUB>, in a similar manner afforded the α-isonitroso ketones, RCOC(=NOH)R′. The mechanisms of these reactions were studied.
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