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Crystal structures and solid state reactions of maleic anhydride and of a cyclohexenone and its photoproduct Hwang, Christine


Two sets of structures were determined by X-ray crystallographic techniques, one of maleic anhydride (2,5-furandione) and the other of 4-phenyl-4-p-bromophenylcyclohex-2-en-1-one and its photoproduct, trans-5-phenyl-6-p-bromophenylbicyclo[3.1.0]hexan-2-one. Analysis of maleic anhydride included a room temperature redetermination of the crystal structure. This was done to improve parameters and simplify comparison of the room temperature and low temperature data. The structure determination at 104k resulted in the location of bonding electrons in the double bond. Thermal motions of both sets of data showed that translational motion was greatest along an axis parallel to the carbonyl bonds. Libration was found to be greatest about this axis also. The second set of structures was done to examine the migration pattern of aryl groups upon irradiation of a diarylcyclohexenone. The major photoproduct was formed by migration of the p-bromophenyl group. The resulting bicyclohexanone had the aryl groups trans to each other.

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