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Nonacarbonyldiiron-, Pentacarbonyliron-, or Hexacarbonylmolybdenum-induced Reactions of 4,5-Polymethylene-substituted 2-Isoxazolines

1985; Oxford University Press; Volume: 58; Issue: 3 Linguagem: Inglês

10.1246/bcsj.58.991

1348-0634

Makoto Nitta, Akihiro Yi, Tomoshige Kobayashi,

Click Chemistry and Applications

Abstract The reaction of 4,5-polymethylene-substituted 2-isoxazolines, 3-phenyl-3a,5,6,7a-tetrahydro-4H-pyrano[3,2-d]isoxazole or 3-phenyl-3a,4,5,6a-tetrahydrofuro[3,2-d]isoxazole, with [Fe2(CO)9], [Fe(CO)5], or [Mo(CO)6] resulted in the formation of 5-hydroxy-1-phenyl-1-pentanone or 4-hydroxy-1-phenyl-1-butanone, via the N–O and C–C bond cleavage of the 2-isoxazoline ring and the subsequent hydrolysis. The similar reaction of 7a-morpholino- and 7a-(1-pyrrolidinyl)-3-phenyl-3a,4,5,6,7,7a-hexahydro-1,2-benzoisoxazoles undergoes the N–O bond cleavage and, the subsequent elimination of the amino group or the C-3a–C-7a bond fission. Although the reaction of 6a-morpholino- and 6a-(1-pyrrolidinyl)-3-phenyl-3a,4,5,6a-tetrahydro-4H-cyclopent[d]isoxazoles with [Mo(CO)6] undergoes the N–O bond cleavage, and the subsequent elimination of the amino group or the C-3a–C-6a bond fission, the reaction of those 2-isoxazolines with [Fe2(CO)9] proceeds very slowly. The mechanisms are proposed for these reactions.