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American Chemical Society, Journal of Organic Chemistry, 7(67), p. 2361-2364, 2002

DOI: 10.1021/jo015887b

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A convenient preparation of functionalized 1,8-dioxygenated naphthalenes from 6-alkoxybenzocyclobutenones

Journal article published in 2002 by Christopher J. Bungard, Jonathan Charles Morris ORCID
This paper was not found in any repository; the policy of its publisher is unknown or unclear.
This paper was not found in any repository; the policy of its publisher is unknown or unclear.

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Abstract

An alternate route for the synthesis of naphthalene building blocks 1-4 has been developed, starting from readily available 6-alkoxybenzocyclobutenones. As thermolysis of a propynylbenzocyclobutenol only provided the naphthalene in low yield, allenyl-substituted benzocyclobutenols were investigated. The desired allenic precursors were prepared by a two-step procedure, which involved hydroxyl-directed reduction of the chloropropargylbenzocyclobutenols obtained from addition of lithiopropargyl chloride to the benzocyclobutenones. Thermolysis of the allenic alcohols gave the desired naphthalenes in good yields. ; Christopher J. Bungard and Jonathan C. Morris ; Copyright © 2002 American Chemical Society