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

Article abstract of DOI:10.1246/bcsj.58.991

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 , , or 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-cyclopentisoxazoles with 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 proceeds very slowly.The mechanisms are proposed for these reactions.