Metalation of o-Halostyrene Oxides. Preparation of Benzocyclobutenols

Eyup Akgün, Margaret B. Glinski, Kasturi L. Dhawan, Tony Durst

Research output: Contribution to journalArticlepeer-review

52 Scopus citations

Abstract

O-Bromo- and O-iodostyrene oxides are converted in fair to good yield to benzocyclobutenols upon treatment with n-BuLi and MgBr2 in THF or ether at -78 °C, followed by warming to room temperature. The reaction involves initial halogen-lithium exchange followed either by MgBr2-initiated opening of the epoxide function to a haloalkoxide or rearrangement of the epoxide function to a ketone or aldehyde followed by cyclization. Benzocyclobutenol formation was not successful in the case of o-halostilbene oxides.

Original languageEnglish (US)
Pages (from-to)2730-2734
Number of pages5
JournalJournal of Organic Chemistry
Volume46
Issue number13
DOIs
StatePublished - Jun 1981

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