Stereospecific double rearrangement of anti-1,5-bishomocycloheptatriene. A rebound pathway of thermal rearrangement involving intermediate geminal hydrogen interchange
Abstract
Through pyrolysis of 7,7-dideuterio-anti-1,5-bishomocycloheptatriene, evidence has been obtained that thermal rearrangement of this ring system proceeds by twofold 1,5-homodienyl rearrangement, the second stage of which involves prior conformational ring inversion and geminal hydrogen interchange.