Chemical consequences of fluorine substitution.: Part 4.: Diels-Alder reactions of fluorinated p-benzoquinones with Dane's diene.: Synthesis of fluorinated D-homosteroids

被引：26

作者：

Essers, M ^{[1
]}

Haufe, G ^{[1
]}

机构：

[1] Univ Munster, Inst Organ Chem, D-48149 Munster, Germany

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 2002年 / 23期

关键词：

D O I：

10.1039/b208001j

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Four fluorinated p-benzoquinones (2) have been reacted with Dane's diene (1) in Diels-Alder reactions and the formed fluorinated D-homosteroids were characterized. The number of products, their stereochemistry and stability depends on the fluorine substitution pattern of the corresponding fluorinated p-benzoquinones. If the p-benzoquinone (2) contains an unfluorinated double bond, this bond reacts faster with diene 1 yielding endo-products selectively. In contrast, [4+2]cycloadditions with 2,6-difluoro (2c) and 2,3,5,6-tetrafluorobenzoquinone (2d) gave the products with exo-orientation of the carbonyl part preferably.

引用

页码：2719 / 2728

页数：10

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