THE REACTION OF QUADRICYCLANE WITH P-ANILS

The reaction of quadricyclane (Q) with p-anils has been generalized in order to define its scope. Tetrafluoro-, tetrachloro-, and tetrabromo -p-benzoquinones in dichloromethane or chloroform, at or below room te mperature give predominant or exclusive formation of the adduct to the C=O bond of the quinone as confirmed by the X-ray structure of the ad duct to chloranil. In the case of DDQ (dicyanodichloro-p-benzoquinone) , the major product is the standard [4+2]-cycloadduct, while the adduc t to the C=O bond is formed as minor product and adds to a second mole cule of quadricyclane to form bis-adduct (4). The structure of the lat ter has also been defined by X-ray analysis.