Nitrosation in organic chemistry. Nitrosolysis, a novel carbon-carbon bond cleavage effected through nitrosation. Nitrosolysis of ketones and ketone acetals

MM Rogic, J Vitrone, MD Swerdloff

Index: Rogic,M.M. et al. Journal of the American Chemical Society, 1977 , vol. 99, p. 1156 - 1171

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Citation Number: 19

Abstract

Abstract: Nitrosation of cyclohexanone with nitrosyl chloride in liquid sulfur dioxide in the presence of methanol, ethanol, or isopropyl alcohol and at least 1 equiv of hydrogen chloride provides the corresponding 2-alkoxy-3-oximinocyclohexenes. However, when the reaction was carried out without the added hydrogen chloride, the alkyl 6- oximinohexanoates are obtained. This novel carbon-carbon bond cleavage was extended ...