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

M Essers, G Haufe

Index: Essers, Michael; Haufe, Guenter Journal of the Chemical Society. Perkin Transactions 1, 2002 , # 23 p. 2719 - 2728

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Citation Number: 30

Abstract

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 ...