Tetrahedron

Fragmentation of tertiary cyclopropanol compounds catalyzed by vanadyl acetylacetonate

…, M Ichinose, Y Ochiai, S Takizawa, A Mokuya, K Okubo…

Index: Kirihara, Masayuki; Kakuda, Hiroko; Ichinose, Motohiro; Ochiai, Yuta; Takizawa, Shinobu; Mokuya, Asuka; Okubo, Kumiko; Hatano, Akihiko; Shiro, Motoo Tetrahedron, 2005 , vol. 61, # 20 p. 4831 - 4839

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Citation Number: 18

Abstract

Tertiary cyclopropanol compounds react with a catalytic amount of vanadyl acetylacetonate in the presence of oxygen affording β-hydroxyketones and β-diketones. For 3-substituted- bicyclo [4.1. 0] alkanols, peroxides are obtained, as are the β-hydroxyketones. Conversely, 2- ethoxycarbonylcyclopropyl silyl ethers produce ethyl γ-oxocarboxylate derivatives given the same reaction conditions.