Journal of the Chemical Society. Perkin transactions I p. 1445 - 1452 (1996)
Update date:2022-08-11
Topics:
Halton, Brian
Kay, Andrew J.
Zhi-mei, Zha
Boese, Roland
Haumann, Thomas
3,6-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 derivatives 15a-e by way of the disilyl compound 14, 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 chemistry of the compounds is described, their spectral data are discussed, and the cyclic voltammetry of 16 is provided.
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