Directed lithiation of some chroman-4-ols

Richard J. Bethune, Christopher D. Gabbutt, Stéphane G R Guinot, John D. Hepworth, B. Mark Heron

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Abstract

Directed lithiation of chroman-4-ols occurs predominantly at C-5 under kinetic control, but at C-8 at higher temperatures. Dehydration and oxidation of the products provides viable routes to 5-substituted 2H-chromenes and chroman-4-ones, respectively. The chroman-4-ones have been converted into novel pyrano[4,3,2-de]phthalazines. 2,2,5,7-Tetramethylchroman-4-ol is preferentially lithiated at the 5-methyl group and leads to the pyrano[2,3,4-de] [1]benzopyran system.

Original languageEnglish
Pages (from-to)1925-1933
Number of pages9
JournalJournal of the Chemical Society, Perkin Transactions 1
Issue number14
DOIs
Publication statusPublished - 1 Dec 1994
Externally publishedYes

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