Directed lithiation of some chroman-4-ols

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

Research output: Contribution to journalArticle

7 Citations (Scopus)

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.

LanguageEnglish
Pages1925-1933
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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Chromans
Phthalazines
Benzopyrans
Dehydration
Oxidation
Kinetics
Temperature

Cite this

Bethune, Richard J. ; Gabbutt, Christopher D. ; Guinot, Stéphane G R ; Hepworth, John D. ; Heron, B. Mark. / Directed lithiation of some chroman-4-ols. In: Journal of the Chemical Society, Perkin Transactions 1. 1994 ; No. 14. pp. 1925-1933.
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Directed lithiation of some chroman-4-ols. / Bethune, Richard J.; Gabbutt, Christopher D.; Guinot, Stéphane G R; Hepworth, John D.; Heron, B. Mark.

In: Journal of the Chemical Society, Perkin Transactions 1, No. 14, 01.12.1994, p. 1925-1933.

Research output: Contribution to journalArticle

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