Reaction of nitrosyl chloride gas with unsaturated steroids.
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概要
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Reaction of nitrosyl chloride gas at 0 °C with 3,5-cholestadiene (<B>1</B>) provided 3,6β-dinitro-5-chloro-5α-cholest-3-ene (<B>4</B>) and with 3α,5-cyclo-5α-cholestan-6-one (<B>2</B>) afforded 3β-chloro-5-nitro-5α-cholestan-6-one (<B>7</B>) and 3β-chloro-6-nitrato-5-cholestene (<B>8</B>). Similar reaction with 6-hydroxylimino 3α,5-cyclo-5α-cholestane (<B>3</B>) gave 3β,6-dichloro-5-cholestene (<B>10</B>), 3β-chloro-6-nitratoimino-5α-cholestane (<B>11</B>) and 3β,5-dichloro-6-nitroimino-5β-cholestane (<B>12</B>). Compound <B>12</B> upon hydrolysis furnished 3β,5-dichloro-5β-cholestan-6-one (<B>14</B>). The structures of these compounds were established on the basis of their spectral properties, and some pertinent chemical transformations. Mechanisms for the formation of some unusual products are discussed.
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著者
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Rafiuddin Ansari
Department of Chemistry, Aligarh Muslim University
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Husain Shakir
Department of Chemistry, Aligarh Muslim University