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Australian Journal of Chemistry Australian Journal of Chemistry Society
An international journal for chemical science
RESEARCH ARTICLE

Flavan derivatives. XXVI. 3(3')-Hydroxyisochromano(4',3':2,3)chromans. Mechanism of formation of these hemiketals from 1'-Oxo-isochromono-(4',3':2,3)chromones

JW Clark-Lewis, EW Della and MM Mahandru

Australian Journal of Chemistry 22(11) 2389 - 2394
Published: 1969

Abstract

Reduction of the lactones of flavonol-2?-carboxylic acids [1?- oxoisochromono-(4?,3?:2,3)chromones] to hemiacetals by lithium aluminium hydride is shown to proceed by fission of the lactone ring accompanied by direct reduction of the chromone carbonyl group without fission of the chromone ring. The intermediate chrom-2-en-4-ols undergo nucleophilic displacement of the allylic (and benzylic) hydroxyl group by hydride ion attack at the 2- and 4-positions. Reduction of 7- methoxyisochromeno(4?,3?:2,3)chromone with lithium aluminium deuteride led to 7-methoxyisochromeno(4?,3?:2,3)chromen with 95% incorporation of two deuterium atoms.

https://doi.org/10.1071/CH9692389

© CSIRO 1969

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