Cyclopentadiene Bisadduct of Tetrafluoro-p-benzoquinone: Its Stereochemistry, Reactivity toward Nucleophiles, And Photochemistry

Article abstract of DOI:10.1021/jo00153a017

The stereochemistry of the cyclopentadiene bisadduct of tetrafluoro-p-benzoquinone (3) is proposed to be endo-trans-exo.This adduct is observed to undergo facile addition of oxygen nucleophiles to one of the carbonyl groups with subsequent addition of the carbonyl adduct to the double bond of the endo-bicycloheptene moiety.Both 3 and the cyclopentadiene bisadduct of p-benzoquinone (5) are observed to undergo photochemical intramolecular oxetane formation.The extremely facile oxetane formation observed with 3 is discussed.