Thermal addition of dibenzoylacetylene to cycloheptatriene and the photo-rearrangement of the thermal adduct |
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| Authors: | S. Lahiri V. Dabral M.V. George |
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| Affiliation: | Department of Chemistry, Indian Institute of Technology, Kanpur 208016, India |
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| Abstract: | The reaction of cycloheptatriene (CHT) with dibenzoylacetylene (DBA), in refluxing toluene gave a mixture of products consisting of 6,7-dibenzoyltricyclo[3.2.2.02.4]nona-6,8-diene 6 and 3,4-dibenzoylbicyclo [3.2.2]nona-2,6,8-triene 7. Neat heating of a mixture of CHT and DBA around 95–100° gave besides, 6 and 7, small amounts of two dimers of DBA. Photolysis of 6 in benzene solution gave a lactonic, rearrangement product. 25. The structures of the various products have been established and reasonable mechanisms for their formation have been suggested. |
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