Notable temperature effect on the stereoselectivity in the photochemical [2+2] cycloaddition reaction (Paternò-Büchi reaction) of 2,3-dihydrofuran-3-ol derivatives with benzophenone

Manabu Abe; Midori Terazawa; Koichi Nozaki; Araki Masuyama; Takashi Hayashi

doi:10.1016/j.tetlet.2006.02.046

Notable temperature effect on the stereoselectivity in the photochemical [2+2] cycloaddition reaction (Paternò-Büchi reaction) of 2,3-dihydrofuran-3-ol derivatives with benzophenone

Manabu Abe^*, Midori Terazawa, Koichi Nozaki, Araki Masuyama, Takashi Hayashi

^*Corresponding author for this work

Department of Chemistry

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

23 Scopus citations

Abstract

A notable temperature effect (nonlinear Eyring plot) on stereoselectivity, trans-configured oxetane 2 versus cis-configured oxetane 2, is reported in the photochemical [2+2] cycloaddition reaction (Paternò-Büchi reaction) of 2,3-dihydrofuran-3-ol derivatives 1 with benzophenone.

Original language	English
Pages (from-to)	2527-2530
Number of pages	4
Journal	Tetrahedron Letters
Volume	47
Issue number	15
DOIs	https://doi.org/10.1016/j.tetlet.2006.02.046
State	Published - 2006/04/10

Keywords

Oxetane
Photochemical [2+2] cycloaddition
Stereoselectivity
The Paternò-Büchi reaction
Triplet diradical

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tetlet.2006.02.046

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@article{afea133cd93e42698f2962bd25129a8a,

title = "Notable temperature effect on the stereoselectivity in the photochemical [2+2] cycloaddition reaction (Patern{\`o}-B{\"u}chi reaction) of 2,3-dihydrofuran-3-ol derivatives with benzophenone",

abstract = "A notable temperature effect (nonlinear Eyring plot) on stereoselectivity, trans-configured oxetane 2 versus cis-configured oxetane 2, is reported in the photochemical [2+2] cycloaddition reaction (Patern{\`o}-B{\"u}chi reaction) of 2,3-dihydrofuran-3-ol derivatives 1 with benzophenone.",

keywords = "Oxetane, Photochemical [2+2] cycloaddition, Stereoselectivity, The Patern{\`o}-B{\"u}chi reaction, Triplet diradical",

author = "Manabu Abe and Midori Terazawa and Koichi Nozaki and Araki Masuyama and Takashi Hayashi",

note = "Funding Information: This work was partially supported by the Ministry of Education, Science, Sports, and Culture, Japan, Grant-in-Aid for Scientific Research (B), No. 17350019, and Mitsubishi Chemical Corporation Fund. ",

year = "2006",

month = apr,

day = "10",

doi = "10.1016/j.tetlet.2006.02.046",

language = "英語",

volume = "47",

pages = "2527--2530",

journal = "Tetrahedron Letters",

issn = "0040-4039",

publisher = "Elsevier Ltd.",

number = "15",

}

Notable temperature effect on the stereoselectivity in the photochemical [2+2] cycloaddition reaction (Paternò-Büchi reaction) of 2,3-dihydrofuran-3-ol derivatives with benzophenone. / Abe, Manabu; Terazawa, Midori; Nozaki, Koichi et al.
In: Tetrahedron Letters, Vol. 47, No. 15, 10.04.2006, p. 2527-2530.

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

TY - JOUR

T1 - Notable temperature effect on the stereoselectivity in the photochemical [2+2] cycloaddition reaction (Paternò-Büchi reaction) of 2,3-dihydrofuran-3-ol derivatives with benzophenone

AU - Abe, Manabu

AU - Terazawa, Midori

AU - Nozaki, Koichi

AU - Masuyama, Araki

AU - Hayashi, Takashi

N1 - Funding Information: This work was partially supported by the Ministry of Education, Science, Sports, and Culture, Japan, Grant-in-Aid for Scientific Research (B), No. 17350019, and Mitsubishi Chemical Corporation Fund.

PY - 2006/4/10

Y1 - 2006/4/10

N2 - A notable temperature effect (nonlinear Eyring plot) on stereoselectivity, trans-configured oxetane 2 versus cis-configured oxetane 2, is reported in the photochemical [2+2] cycloaddition reaction (Paternò-Büchi reaction) of 2,3-dihydrofuran-3-ol derivatives 1 with benzophenone.

AB - A notable temperature effect (nonlinear Eyring plot) on stereoselectivity, trans-configured oxetane 2 versus cis-configured oxetane 2, is reported in the photochemical [2+2] cycloaddition reaction (Paternò-Büchi reaction) of 2,3-dihydrofuran-3-ol derivatives 1 with benzophenone.

KW - Oxetane

KW - Photochemical [2+2] cycloaddition

KW - Stereoselectivity

KW - The Paternò-Büchi reaction

KW - Triplet diradical

UR - http://www.scopus.com/inward/record.url?scp=33644912033&partnerID=8YFLogxK

U2 - 10.1016/j.tetlet.2006.02.046

DO - 10.1016/j.tetlet.2006.02.046

M3 - 学術論文

AN - SCOPUS:33644912033

SN - 0040-4039

VL - 47

SP - 2527

EP - 2530

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 15

ER -

Notable temperature effect on the stereoselectivity in the photochemical [2+2] cycloaddition reaction (Paternò-Büchi reaction) of 2,3-dihydrofuran-3-ol derivatives with benzophenone

Abstract

Keywords

ASJC Scopus subject areas

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