Synthesis of (R)-4,5-dihydro-3H-dinaphtho-[2,1-c:1',2'-e]-selenepin oxide and preliminary studies on its use in the oxidation of sulfides

Article abstract of DOI:10.1080/00397910008087448

The first synthesis (R)-4,5-dihydro-3H-dinaphtho-[2,1-c:1',2'-e]- selenepin oxide 1 has been achieved from (R)-(+)-1,1'-bi-2-naphthol, which in turn was obtained by resolution of rac-1,1'-bi-2-naphthol. Palladium catalyzed alkoxy-carbonylation of ditriflate 4 gave dimethyl ester 5 which was then reduced and the resultant diol converted to key intermediate chloride 8. Cyclization with sodium selenolate gave novel enantiomerically pure selenide 9, which upon oxidation yielded the desired selenoxide (R)-1. Preliminary studies on the oxidation of sulfides to sulfoxides using 1 and 2,2,2-trifluoroethane sulfonic acid are also described.

Full text of DOI:10.1080/00397910008087448

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Synthetic Communications: An
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Synthesis of (R)-4,5-
Dihydro-3H-Dinaphtho-[2,1-
c:1',2'-e]Selenepin Oxide and
Preliminary Studies on Its Use
in the Oxidation of Sulfides
David J. Procter a & Christopher M. Rayner a
a School of Chemistry , University of Leeds , Leeds,
LS2 9JT, U.K. E-mail:
Published online: 04 Dec 2007.
To cite this article: David J. Procter & Christopher M. Rayner (2000) Synthesis of
(R)-4,5-Dihydro-3H-Dinaphtho-[2,1-c:1',2'-e]Selenepin Oxide and Preliminary Studies
on Its Use in the Oxidation of Sulfides, Synthetic Communications: An International
Journal for Rapid Communication of Synthetic Organic Chemistry, 30:16, 2975-2987,
DOI: 10.1080/00397910008087448
To link to this article: http://dx.doi.org/10.1080/00397910008087448
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