Thallium(III) nitrate oxidation of chromens: cis-dihydroxylation and dialkoxylation
- 1 January 1983
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- No. 4,p. 883-887
- https://doi.org/10.1039/p19830000883
Abstract
The oxidation of the chromens (6) and (10) with thallium(III) nitrate is described. In the case of the 2-methyl-2H-chromen (6) oxidation in aqueous dioxan gave a single cis-1,2-diol (7), unexpectedly arising from initial thalliation syn to the 2-methyl. The product stereochemistry was determined by single-crystal X-ray analysis, using direct methods. Rationalisation is proposed. With the 2,2-dimethylchromen (10), oxidation in methanol gave only the cis-dimethoxychroman (11); similar reactions were observed in other hydroxylic solvents. In ethane- 1,2-diol the fused dioxan (18) was obtained, but in poor yield.This publication has 2 references indexed in Scilit:
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