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The Reaction of Isobenzofulvenes with Heterodienophiles: A Simple Route to Indeno[a]heterocycles and 2-Heterosubstituted benzonorbornanes

Ronald N. Warrener,* Peter A. Harrison, Richard A. Russell

Centre for Molecular Architecture, Central Queensland University, Rockhampton, Queensland, 4702, AUSTRALIA

The reaction of 6,6-dimethylisobenzofulvene with heterodienophile has been investigated. In all cases, the Diels-Alder [4p+2p] adduct is formed initially. The 2-oxabenzo norbornanes and 2-thiabenzonorbornanes are shown to undergo rearrangement to indeno[a]heterocycles. Various indeno[a]furans and indeno[a]thiophenes have been isolated and characterised by spectral means. The 2-azabenzonorbornanes are more stable, thus allowing chemical modification of the bicyclic ring.

Typical Reaction

Representative reaction products

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