SUBSTITUENT EFFECTS ON HYDROCARBON CHAIN CYCLIZATION PROBED BY AN INTRA-MOLECULAR PHOTO-CHEMICAL REACTION

被引：7

作者：

MAHARAJ, U

WINNIK, MA

DORS, B

SCHAFER, HJ

机构：

[1] UNIV TORONTO,ERINDALE COLL,MISSISSAUGA L5L 1C6,ONTARIO,CANADA

[2] UNIV TORONTO,LASH MILLER CHEM LABS,DEPT CHEM,TORONTO M5S 1A1,ONTARIO,CANADA

[3] UNIV MUNSTER,DEPT ORGAN CHEM,D-4400 MUNSTER,FED REP GER

来源：

MACROMOLECULES | 1979年 / 12卷 / 05期

关键词：

D O I：

10.1021/ma60071a023

中图分类号：

O63 [高分子化学（高聚物）];

学科分类号：

070305 ; 080501 ; 081704 ;

摘要：

The molecules benzophenone-4-CO2(CH2)nCH3(IV) undergo an intramolecular hydrogen abstraction reaction. So, too, do the molecules benzophenone-4-CO2-X'-O2C(CH2)12CH3, where the substituents (I, X' = -CH2CH2-, II, X' = trans-1, 2-cyclohexyl, and III, X' = 1, 2-benzenyl) impose conformational constraints on the chain which are predicted to increase the cyclization probability of the chain. Flash photolysis measurements indicate that cyclization is enhanced by factors of 2.5, 6, and 9 for I, II, and III, respectively, over the 17-carbon ester of IV. © 1979, American Chemical Society. All rights reserved.

引用

页码：905 / 909

页数：5

共 28 条

[1]

[Anonymous], CONFORMATIONAL PROPE

[2]

BRESLOW R, 1978, J AM CHEM SOC, V100, P1213, DOI 10.1021/ja00472a030

[3] CENTENARY LECTURE - BIOMIMETIC CHEMISTRY [J].