Geometrically specific hydrogen transfer in the reaction of terminally alkyl-substituted 1,3-dienes with 1,4-quinones

被引：10

作者：

Cameron, DW ^{[1
]}

Heisey, RM ^{[1
]}

机构：

[1] Univ Melbourne, Sch Chem, Parkville, Vic 3010, Australia

来源：

AUSTRALIAN JOURNAL OF CHEMISTRY | 2000年 / 53卷 / 02期

关键词：

dienes; quinones; cycloaddition; hydrogen transfer;

D O I：

10.1071/CH00027

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Reaction of certain geometrically defined 1,1-dioxy-4-alkyl- and -4,4-dialkyl-substituted buta-1,3-dienes with halogenated quinones does not involve Diels-Alder or Michael addition chemistry. Instead, rapid competitive oxidation of the dienes to give 2,4-dienoate esters was observed. This new reaction involves strong spatial association between diene and quinone, hydrogen being transferred specifically from the (4E)-alkyl group. Its scope is compared with addition of the same terminally substituted dienes towards the reactive non-quinonoid dienophile tetracyanoethylene.

引用

页码：109 / 121

页数：13

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