Electronic effects in the regioselectivity of the singlet oxygen and 4-methyl-1,2,4-triazoline-3,5-dione ene reactions with isobutenylarenes

被引：9

作者：

Alberti, MN ^{[1
]}

Vougioukalakis, GC ^{[1
]}

Orfanopoulos, M ^{[1
]}

机构：

[1] Univ Crete, Dept Chem, Iraklion 71409, Crete, Greece

来源：

TETRAHEDRON LETTERS | 2003年 / 44卷 / 05期

关键词：

singlet oxygen; ene reactions; triazolinediones;

D O I：

10.1016/S0040-4039(02)02783-1

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The regioselectivity of the ene pathway in the photooxidation of several 1-aryl-2-methylpropenes, as probed by stereoselective deuterium-labeling, depends on the electronic nature of the para phenyl-substituents. The reaction of the same array of alkenylarenes with 4-methyl-1,2,4-triazoline-3,5-dione (MTAD) gives ene products with an impressive >97% allylic hydrogen abstraction from the more substituted side of the alkene. (C) 2003 Elsevier. Science Ltd. All rights reserved.

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页码：903 / 905

页数：3

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