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Directed lithiation of some chroman-4-ols

Bethune, Richard J., Gabbutt, Christopher D., Guinot, Stephane G. R., Hepworth, John D. and Heron, B. Mark (1994) Directed lithiation of some chroman-4-ols. Journal of the Chemical Society, Perkin Transactions 1 (14). pp. 1925-1933. ISSN 0300-922X

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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.

Item Type: Article
Subjects: Q Science > Q Science (General)
Q Science > QD Chemistry
Schools: School of Applied Sciences
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Depositing User: Sharon Beastall
Date Deposited: 20 Sep 2012 11:31
Last Modified: 28 Aug 2021 11:21


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