[2+2] photodimerization of 1-aryl-4-pyridylbutadienes through cation-π interactions

被引：18

作者：

Yamada, Shinji ^{[1
]}

Azuma, Yuka ^{[1
]}

Aya, Kanae ^{[1
]}

机构：

[1] Ochanomizu Univ, Fac Sci, Dept Chem, Bunkyo Ku, Tokyo 1128610, Japan

来源：

TETRAHEDRON LETTERS | 2014年 / 55卷 / 17期

关键词：

Cation-pi interaction; Cope rearrangement; 2+2] photodimerization; Catalysis; Cyclooctadiene; SOLID-STATE; PHOTOCHEMISTRY; REARRANGEMENT; TOPOCHEMISTRY; BUTADIENES;

D O I：

10.1016/j.tetlet.2014.03.036

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Irradiation of 1-aryl-4-pyridylbutadienes in the presence of 1 equiv of HCl produced syn and anti head-to-tail dimers, among a number of possible dimers, whereas irradiation in the absence of HCl gave a complex mixture. This indicated that the acid serves as a catalyst for the regio- and stereoselective [2+2] photodimerization of 1-aryl-4-pyridylbutadienes through cation it interactions between the pyridinium and aromatic rings. The produced synHT dimers underwent Cope rearrangement to produce cyclooctadienes, and they were in equilibrium at a ratio of 85:15 in CDCl3. (C) 2014 Elsevier Ltd. All rights reserved.

引用

页码：2801 / 2804

页数：4

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