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Umwandlung von Aldehyden in 2-monosubstituierte Aziridine. Reduktion von α-Chlor, Brom- und Sulfonyloxynitilen mit Lithiumaluminiumhydrid

1970; Oxford University Press; Volume: 43; Issue: 5 Linguagem: Inglês

10.1246/bcsj.43.1443

1348-0634

Kunihiro Ichimura, Masaki Ohta,

Chemical Synthesis and Reactions

Abstract The reductive cyclization of α-chloro, bromo- and sulfonyloxycarbonitriles are described. α-Chlorocarbonitriles were reduced by lithium aluminum hydride to afford aziridines in sufficient yields. The Walden inversion was found to take place in the cource of the reductive cyclization of S-α-chloroisocapronitrile. We have found the two-step conversion of aldehydes to 2-mono-substituted aziridines which consists of treating aldehydes with benzenesulfonyl chloride and alkali cyanide to form α-benzenesulfonyloxycarbonitriles which are reduced by lithium aluminum hydride to the corresponding aziridines. The reduction of α-bromocarbonitriles with the hydride yielded prim. amines together with the aziridines.