Preparation and Diels-Alder reactions of the [n](1, 4) naphthalenophanes. Isolation of a paddlane derivative containing the tricyclo [14.2. 2.21, 6] docosane ring system

KB Wiberg, MJ O'Donnell

Index: Wiberg,K.B.; O'Donnell,M.J. Journal of the American Chemical Society, 1979 , vol. 101, # 22 p. 6660 - 6666

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Citation Number: 25

Abstract

Abstract: The [n](1, 4) naphthalenophanes (n= 8, 9, IO, and 14) were prepared and treated with dicyanoacetylene. The major product in all cases was the Diels-Alder adduct at the unsubstitutcd aromatic ring. The paddlane. 2.3-dicyano-l, 4-etheno-I, 4-dihydro-l, 4- tetradecanonaphthalene (28), a derivative of the parent hydrocarbon, tricycle [1 4.2. 2.? 1, 6] docosane, was isolated as a minor product from the reaction of [14](1, 4) ...