Studies in the cycloproparene series: oxygen-containing 1H-cyclopropa [b] naphthalenes and their methylidene derivatives

…, AJ Kay, Z Zhi-Mei, R Boeseb, T Haumann

Index: Halton, Brian; Kay, Andrew J.; Zhi-mei, Zha; Boese, Roland; Haumann, Thomas Journal of the Chemical Society - Perkin Transactions 1, 1996 , # 12 p. 1445 - 1452

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Citation Number: 22

Abstract

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 ...