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Kinetic stabilization of the o-quinoidal 3,4-benzotropone system.

Kinetic stabilization of the o-quinoidal 3,4-benzotropone system was investigated. The parent 3,4-benzotropone undergoes rapid [pi8 + pi10] dimerization in fluid solution even at -78 degree C while triptycene-fused derivative having a tert-butyl group at the C6 position of the tropone moiety was found to be stable indefinitely under similar conditions. The relative importance of the triptycene moiety and the tert-butyl group in for the kinetic stabilization was evaluated.