Chemische Berichte

Cope??Umlagerungen Donor??substituierter 1, 5??Hexadiene

M Dollinger, W Henning, W Kirmse

Index: Dollinger, Michael; Henning, Wolfgang; Kirmse, Wolfgang Chemische Berichte, 1982 , vol. 115, # 6 p. 2309 - 2325

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Citation Number: 21

Abstract

Abstract Alkoxy-, Alkylthio-und Dialkylaminogruppen in 3-Position des 1, 5-Hexadiens und in 2-Position des 3, 3-Dimethyl-1, 5-hexadiens haben relativ geringen Einfluß auf die Cope- Umlagerung (Erhöhung der Reaktionsgeschwindigkeit maximal um den Faktor 60, ΔE a maximal 5.5 kcal/mol= 23 kJ/mol). Die Substituenteneffekte sind mit einem diradikalischen Mechanismus besser vereinbar als mit einer konzertierten sigmatropen Umlagerung.

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