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

被引：16

作者：

Abe, M

Terazawa, M

Nozaki, K

Masuyama, A

Hayashi, T

机构：

[1] Osaka Univ, Grad Sch Engn, Dept Appl Chem, Suita, Osaka 5650871, Japan

[2] Osaka Univ, Grad Sch Sci, Dept Chem, Toyonaka, Osaka 5600043, Japan

来源：

TETRAHEDRON LETTERS | 2006年 / 47卷 / 15期

关键词：

the Paterno-Buchi reaction; photochemical [2+2] cycloaddition; stereoselectivity; oxetane; triplet diradical;

D O I：

10.1016/j.tetlet.2006.02.046

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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 (Paterno-Buchi reaction) of 2,3-dihydrofuran-3-ol derivatives 1 with benzophenone. (c) 2006 Elsevier Ltd. All rights reserved.

引用

页码：2527 / 2530

页数：4

共 37 条

[1] Mechanism of stereo- and regioselectivity in the Paterno-Buchi reaction of furan derivatives with aromatic carbonyl compounds: Importance of the conformational distribution in the intermediary triplet 1,4-diradicals [J].