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

Research output: Contribution to journal › Article › peer-review

27 Citations (Scopus)

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.

Original language	English
Pages (from-to)	4831-4839
Number of pages	9
Journal	Tetrahedron
Volume	61
Issue number	20
DOIs	https://doi.org/10.1016/j.tet.2005.03.033
Publication status	Published - 2005 May 16
Externally published	Yes

Keywords

Cyclopropanes
Fragmentation reactions
Peroxides
Vanadium compounds

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

Access to Document

10.1016/j.tet.2005.03.033

Cite this

@article{96cc3d9cbd7945f69053a4684920fee1,

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",

language = "English",

volume = "61",

pages = "4831--4839",

journal = "Tetrahedron",

issn = "0040-4020",

publisher = "Elsevier Limited",

number = "20",

}

TY - JOUR

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

UR - http://www.scopus.com/inward/record.url?scp=17844383740&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=17844383740&partnerID=8YFLogxK

U2 - 10.1016/j.tet.2005.03.033

DO - 10.1016/j.tet.2005.03.033

M3 - Article

AN - SCOPUS:17844383740

SN - 0040-4020

VL - 61

SP - 4831

EP - 4839

JO - Tetrahedron

JF - Tetrahedron

IS - 20

ER -

Fragmentation of tertiary cyclopropanol compounds catalyzed by vanadyl acetylacetonate

Abstract

Keywords

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this