Scope and Limitations of a New Highly Selective Synthesis of Unsymmetrical Monomers for the Synthesis of Precursors toward Poly(arylenevinylene)s

• Published in: Journal of organic chemistry Vol. 65; no. 2; pp. 284 - 289
• Main Authors: Van Der Borght, Michael, Vanderzande, Dirk, Adriaensens, Peter, Gelan, Jan
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society 28.01.2000; Amer Chemical Soc
• Subjects: Chemistry; Chemistry, Organic; Physical Sciences; Science & Technology; OXIDATION; SULFOXIDES; T-BUTYL HYDROPEROXIDE; POLY(1,4-PHENYLENEVINYLENES); CHEMICAL-VAPOR-DEPOSITION; METATHESIS POLYMERIZATION; SULFIDES; HYDROGEN-PEROXIDE; POLY(P-PHENYLENE VINYLENE); DERIVATIVES
• ISSN: 0022-3263; 1520-6904
• DOI: 10.1021/jo990111k

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.