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Issue 0, 1972
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1,2-Dihydrobenzocyclobutene (‘benzocycflobutene’): lithiation, and the preparation of some 3-substituted derivatives

Abstract

Treatment of 1,2-dihydrobenzocyclobutene (‘benzocyclobutene’) with n-butyl-lithium–tetramethylethylenediamine in ether gives a mixture of the 1-, 3-, and 4-lithio- and 1,2-dilithio-species; initially the 1- and 3-lithio-species are mainly formed, in roughly equal amounts, but if the reaction is prolonged the 3-lithio-derivative predominates. Treatment of the mixture with chlorotrimethyl-silane or -stannane has given samples of 1- and 3-trimethylsilyl- and -stannyl-1,2-dihydrobenzocyclobutene and 1,2-bis(trimethylsilyl)-1,2-dihydrobenzocyclobutene. Cleavage of the 3-trimethyl-silyl- and -stannyl derivatives with bromine and with iodine monochloride has given 3-bromo- and 3-iodo-1,2-dihydrobenzocyclobutene, and cleavage of the 3-trimethylsilyl compound with mercury-(II) acetate has given the 3-acetoxymercuri-compound.

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Article information


J. Chem. Soc., Perkin Trans. 1, 1972, 2481-2484
Article type
Paper

1,2-Dihydrobenzocyclobutene (‘benzocycflobutene’): lithiation, and the preparation of some 3-substituted derivatives

C. Eaborn, A. A. Najam and D. R. M. Walton, J. Chem. Soc., Perkin Trans. 1, 1972, 2481
DOI: 10.1039/P19720002481

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