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The role of the oxygen atom in benzylic hydroxylations of naphthopyrans

Giles, R.G.F. and Green, I.R. (1990) The role of the oxygen atom in benzylic hydroxylations of naphthopyrans. South African Journal of Chemistry, 43 (3-4). pp. 96-100.

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Benzylic hydroxylation of 5,1 0-dimethoxy-2,2-dimethylnaphtho[2,3-bj pyran followed by oxidative demethylation afforded the naturally occurring 4-hydroxy-a-lapachone as its racemate, in 72% yield. Treatment of trans-1 ,2,3,4-tetrahydro-5, 1 0-dimethoxy-1 ,3-dimethylanthracene under similar conditions failed to hydroxylate the 4-position. It would thus appear that the naphthopyran ring-oxygen facilitates benzylic hydroxylations at C(4) in both naphtho[2,3-bj- and naphtho[2,3-cJpyrans.

Item Type: Journal Article
Publisher: South African Bureau for Scientific Publications
Copyright: © 1990 South African Chemical Institute (SACI)
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