Tetrahedron

Dihydroaromatic compounds in the Diels-Alder reaction—IV: Synthesis of bicyclic ketones

I Alfaro, W Ashton, KL Rabone, NAJ Rogers

Index: Alfaro,I. et al. Tetrahedron, 1974 , vol. 30, p. 559 - 569

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Citation Number: 21

Abstract

The in situ isomerisation and Diels-Alder reaction with 2-acetoxyacrylonitrile, of 2, 5- dihydroanisole, leads to the adducts (1) which may be used as starting point for the synthesis of a number of bicyclo [2, 2, 2] octenones, bicyclo [3, 2, 1] octenones and bicyclo [3, 2, 2] nonenones. Under similar conditions, 2, 5-dihydrotoluene reacts via an ene-reaction to produce, after hydrolysis, the acetylcyclohexadiene (27). The base-catalysed ...