ORBITAL INTERACTIONS .5. THROUGH-SPACE EFFECTS OF SUBSTITUENTS ON THE REACTIVITY OF A DOUBLE-BOND TOWARD DIELS-ALDER AND EPOXIDATION REACTIONS

被引：36

作者：

PADDONROW, MN ^{[1
]}

PATNEY, HK ^{[1
]}

WARRENER, RN ^{[1
]}

机构：

[1] AUSTRALIAN NATL UNIV,DEPT CHEM,CANBERRA 2600,ACT,AUSTRALIA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1979年 / 44卷 / 22期

关键词：

D O I：

10.1021/jo01336a031

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A series of 9-substituted octahydrodimethanonaphthalenes (17a-f) have been synthesized, and the kinetics of their Diels-Alder cycloaddition reactions with 3, 6-di(2'-pyridyl)-s-tetrazine (2) have been determined. The rate of reaction of the syn alcohol 17d is strongly solvent dependent, being some 500 times faster in Me2SO than in CHC13 solution. This result is explained in terms of the different conformational preferences of the hydroxyl group in the two solvents, being intramolecularly H bonded (26) in CHCl3and intermolecularly H bonded (27) in Me2SO. © 1979, American Chemical Society. All rights reserved.

引用

页码：3908 / 3917

页数：10

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