Tetrahedron

Photochemically generated bicyclic ortho-quinodimethanes: Photo-enolization of bicyclic aldehydes and ketones

TJ Connolly, T Durst

Index: Connolly, Terrence J.; Durst, Tony Tetrahedron, 1997 , vol. 53, # 47 p. 15969 - 15982

Full Text: HTML

Citation Number: 12

Abstract

A photoenolization route to bicyclic ortho-quinodimethanes was investigated. Bicyclic photoenols were trapped in an intermolecular fashion with various dienophiles for the first time. All ortho-quinodimethane precursors were prepared via a selective route commencing with 1-indanol, α-tetralol and 1-benzosuberone. Irradiation afforded the E-photoenols exclusively which were trapped with equal efficiency except that derived from indane-4- ...