Strained aromatic systems. Synthesis of cyclopropabenzocyclobutenes, cyclopropanaphthocylobutenes, and related compounds

D Davalian, PJ Garratt, W Koller…

Index: Davalian, Dariush; Garratt, Peter J.; Koller, Wolfgang; Mansuri, Muzammil M. Journal of Organic Chemistry, 1980 , vol. 45, # 21 p. 4183 - 4193

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Citation Number: 17

Abstract

The diene 9, prepared in four steps from diethyl cyclohex-4-ene-1, 2-dicarboxylate, was converted into cyclopropa [4, 5] benzocyclobutene (3) by photoirradiation to the cyclobutene 20 followed by treatment with KO-t-Bu and into cyclopropa [e] cyclobuta [blnaphthalene (45) by Diels-Alder addition to diethyl cyclobutene-1, 2-dicarboxylate, oxidation, and treatment with KO-t-Bu. Attempts to convert 9 into cyclopropa [b] anthracene were unsuccessful. The ...

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