Studies in the cycloproparene series: oxygen-containing 1H-cyclopropa[b]naphthalenes and their methylidene derivatives.
In: Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry, (1996) ; Nr. 12, S. 1445-1452
Zeitschriftenaufsatz / Fach: Chemie
3,5-Dimethoxy-1H-cyclopropa[b]naphthalene 4 is available from 1,4-benzoquinone in four steps in 27-28% overall yield. The diether 4 provides a range of methylidene derivs. by way of a disilyl compd., and is efficiently demethylated by cerium(IV) ammonium nitrate to provide 1H-cyclopropa[b]naphthalene-3,6-dione 16 (85%) whose crystal structure is reported. Quinone 16 is the first stable cyclopropaquinone but it resists conversion into a 1-C exocyclic olefin. The chem. of the compds. is described, their spectral data are discussed, and the cyclic voltammetry of 16 is provided.