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A novel titanium tetrachloride-induced rearrangement of an enantiopure 4-naphthyldioxolane. The possible role of titanium in the umpolung of tosyloxy and chlorine

Giles, R.G.F. and McManus, J.D. (2009) A novel titanium tetrachloride-induced rearrangement of an enantiopure 4-naphthyldioxolane. The possible role of titanium in the umpolung of tosyloxy and chlorine. Tetrahedron Letters, 50 (46). pp. 6361-6363.

Link to Published Version: http://dx.doi.org/10.1016/j.tetlet.2009.08.107
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Abstract

The rearrangement of (2′S,4′R,5′S)-2-(2′,5′-dimethyl-1′,3′-dioxolan-4′-yl)-4,5,7-trimethoxynaphthalen-1-yl 4″-methylbenzenesulfonate with titanium(IV) chloride affords (1R,3S,4R)-10-chloro-6,7,9-trimethoxy-1,3-dimethyl-3,4-dihydro-4-hydroxynaphtho[1,2-c]pyran in good yield. This transformation is characterized by two unusual aromatic substitution reactions in that, in one, tosyloxy is lost and, in the other, aromatic chlorination occurs with titanium(IV) chloride as the source of chlorine.

Publication Type: Journal Article
Murdoch Affiliation: School of Chemical and Mathematical Science
Publisher: Elsevier BV
Copyright: © 2009 Elsevier Ltd.
URI: http://researchrepository.murdoch.edu.au/id/eprint/6800
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