Topochemical photodimerization of (E)-3-benzylidene-4-chromanone derivatives from β-type structures directed by halogen groups

被引：26

作者：

Cheng, Xue-Ming ^{[1
]}

Huang, Zhi-Tang ^{[1
]}

Zheng, Qi-Yu ^{[1
]}

机构：

[1] Chinese Acad Sci, Inst Chem, CAS Key Lab Mol Recognit & Funct, Beijing Natl Lab Mol Sci, Beijing 100190, Peoples R China

来源：

TETRAHEDRON | 2011年 / 67卷 / 47期

基金：

中国国家自然科学基金;

关键词：

Solid reaction; Photodimerization; (E)-3-Benzylidene-4-chromanone; Halogen group; Crystal engineering; SOLID-STATE; ALPHA; BETA-UNSATURATED KETONES; PHOTOCHEMICAL-REACTIONS; CRYSTAL; REACTIVITY; ACID; CONSTRUCTION; TEMPLATE; ACRIDINE; DESIGN;

D O I：

10.1016/j.tet.2011.09.087

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Halogen substituent plays an important role in the crystalline packing of aromatic compounds. The [2+2] photocycloaddition of (E)-3-benzylidene-4-chromanones in the crystalline state was investigated, and halogen substitution has been adopted to organize molecules with proper arrangement for photodimerization. Not halogen bonds, but the electron-withdrawing property of halogen atoms can enhance the face-to-face pi-pi interactions. Therefore, F, Cl or Br substitution at the para position of phenyl gave rise to almost the same beta-structures with face-to-face pi-stacking. Only resulted beta-structures can undergo photodimerization, which gave the syn-HH (syn-head-to-head) products with high regio-/stereoselectivity. (C) 2011 Elsevier Ltd. All rights reserved.

引用

页码：9093 / 9098

页数：6

共 64 条

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