Fragmentation of tertiary cyclopropanol compounds catalyzed by vanadyl acetylacetonate

Masayuki Kirihara; Hiroko Kakuda; Motohiro Ichinose; Yuta Ochiai; Shinobu Takizawa; Asuka Mokuya; Kumiko Okubo; Akihiko Hatano; Motoo Shiro

doi:10.1016/j.tet.2005.03.033

Fragmentation of tertiary cyclopropanol compounds catalyzed by vanadyl acetylacetonate

Masayuki Kirihara, Hiroko Kakuda, Motohiro Ichinose, Yuta Ochiai, Shinobu Takizawa, Asuka Mokuya, Kumiko Okubo, Akihiko Hatano, Motoo Shiro

研究成果: Article › 査読

24 被引用数 (Scopus)

抄録

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.

本文言語	English
ページ（範囲）	4831-4839
ページ数	9
ジャーナル	Tetrahedron
巻	61
号	20
DOI	https://doi.org/10.1016/j.tet.2005.03.033
出版ステータス	Published - 2005 5月 16
外部発表	はい

ASJC Scopus subject areas

生化学
創薬
有機化学

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10.1016/j.tet.2005.03.033

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title = "Fragmentation of tertiary cyclopropanol compounds catalyzed by vanadyl acetylacetonate",

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.",

keywords = "Cyclopropanes, Fragmentation reactions, Peroxides, Vanadium compounds",

author = "Masayuki Kirihara and Hiroko Kakuda and Motohiro Ichinose and Yuta Ochiai and Shinobu Takizawa and Asuka Mokuya and Kumiko Okubo and Akihiko Hatano and Motoo Shiro",

year = "2005",

month = may,

day = "16",

doi = "10.1016/j.tet.2005.03.033",

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T1 - Fragmentation of tertiary cyclopropanol compounds catalyzed by vanadyl acetylacetonate

AU - Kirihara, Masayuki

AU - Kakuda, Hiroko

AU - Ichinose, Motohiro

AU - Ochiai, Yuta

AU - Takizawa, Shinobu

AU - Mokuya, Asuka

AU - Okubo, Kumiko

AU - Hatano, Akihiko

AU - Shiro, Motoo

PY - 2005/5/16

Y1 - 2005/5/16

N2 - 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.

AB - 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.

KW - Cyclopropanes

KW - Fragmentation reactions

KW - Peroxides

KW - Vanadium compounds

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U2 - 10.1016/j.tet.2005.03.033

DO - 10.1016/j.tet.2005.03.033

M3 - Article

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EP - 4839

JO - Tetrahedron

JF - Tetrahedron

SN - 0040-4020

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ER -

Fragmentation of tertiary cyclopropanol compounds catalyzed by vanadyl acetylacetonate

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