Murdoch University Research Repository

Welcome to the Murdoch University Research Repository

The Murdoch University Research Repository is an open access digital collection of research
created by Murdoch University staff, researchers and postgraduate students.

Learn more

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.

[img]
Preview
PDF - Authors' Version
Download (365kB) | Preview
Link to Published Version: http://dx.doi.org/10.1016/j.tetlet.2009.08.107
*Subscription may be required

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.

Item 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
Item Control Page Item Control Page

Downloads

Downloads per month over past year