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Paper | Regular issue | Vol 41, No. 4, 1995, pp.665-673
Published online, 1st January, 1970
DOI: 10.3987/COM-93-6498
The Reaction of Quadricyclane with p-Anils

Fabrizio Fabris, Ottorino De Lucchi, Giovanni Valle, and Sergio Cossu

*Dipartimento di Chimica, Università di Venezia, Dorsoduro 2137, I-30123 Venezia, Italy

Abstract

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 temperature 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 adduct to chloranil. In the case of DDQ (dicyanodichloro-p-benzoquinone), the major product is the standard [4+2]-cycloadduct, while the adduct to the C=O bond is formed as minor product and adds to a second molecule of quadricyclane to form bis-adduct (4). The structure of the latter has also been defined by X-ray analysis.