Scope and limitations of a new highly selective synthesis of unsymmetrical monomers for the synthesis of precursors toward poly(arylenevinylene)s

Van Der Borght M; D Vanderzande; P Adriaensens; J Gelan

doi:10.1021/jo990111k

Scope and limitations of a new highly selective synthesis of unsymmetrical monomers for the synthesis of precursors toward poly(arylenevinylene)s

J Org Chem. 2000 Jan 28;65(2):284-9. doi: 10.1021/jo990111k.

Authors

Van Der Borght M¹, D Vanderzande, P Adriaensens, J Gelan

Affiliation

¹ Laboratory for Organic and Polymer Chemistry, Division Chemistry, Institute for Material Research, Limburg University, University Campus, B-3590 Diepenbeek, Belgium.

PMID: 10813931
DOI: 10.1021/jo990111k

Abstract

In our laboratory a precursor route to poly(p-phenylenevinylene) derivatives is developed in which unsymmetrically substituted p-xylene derivatives, possessing a benzylic sulfinylalkyl group, are used as monomers. Because of this unsymmetry, we were forced to investigate thoroughly the synthesis of these sulfoxides, as we start from symmetric and readily accessible molecules, namely, bis(halomethyl)-p-xylene derivatives. In a former publication, a new extremely effective route for the production of these unsymmetrically substituted sulfinyl monomers was presented. This paper expands upon these previously reported results. To examine the scope and limitations of this elegant route, this new method was applied to the synthesis of various derivatives not included in the initial work.