Highly regioselective 1,2-addition of alkoxybenzyl Grignard reagents to α-oxoketene dithioacetals: a facile regiocontrolled synthesis of alkoxynaphthalenes and their condensed analogs via aromatic annelation

Mehta, Barun K. ; Nandi, Sukumar ; Ila, H. ; Junjappa, H. (1999) Highly regioselective 1,2-addition of alkoxybenzyl Grignard reagents to α-oxoketene dithioacetals: a facile regiocontrolled synthesis of alkoxynaphthalenes and their condensed analogs via aromatic annelation Tetrahedron, 55 (44). pp. 12843-12852. ISSN 0040-4020

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Official URL: http://linkinghub.elsevier.com/retrieve/pii/S00404...

Related URL: http://dx.doi.org/10.1016/S0040-4020(99)00757-7

Abstract

4-Methoxybenzyl- (A), 3,4-dimethoxybenzyl- (B) and 3,4-methylenedioxybenzyl- (C) Grignard reagents are shown to undergo regioselective 1,2-addition with various acyclic and cyclic -oxoketene dithioacetals to afford carbinol dithioacetals which on BF3.Et2O catalyzed cyclization yield alkoxynaphthalenes and their condensed derivatives in a highly regiocontrolled manner.

Item Type:Article
Source:Copyright of this article belongs to Elsevier Science.
Keywords:Ketene Dithioacetals; Grignard Reagents; Aromatic Annelation; Alkoxynaphthalenes
ID Code:15295
Deposited On:13 Nov 2010 12:59
Last Modified:03 Jun 2011 04:55

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