Synthesis 2011(2): 303-315  
DOI: 10.1055/s-0030-1258352
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis and Characterization of Donor-Functionalized N,S-Compounds Containing the ortho-Aminothiophenol Motif

Edward D. Cross, Usman A. Shehzad, Samantha M. Lloy, Adam R. C. Brown, Todd D. Mercer, Daniel R. Foster, Beth L. McLellan, Alexander R. Murray, Margaret A. English, Matthias Bierenstiel*
Department of Chemistry, Cape Breton University, 1250 Grand Lake Road, Sydney, NS, B1P 6L2, Canada
Fax: +1(902)5631899; e-Mail: matthias_bierenstiel@cbu.ca;
Further Information

Publication History

Received 5 October 2010
Publication Date:
03 December 2010 (eFirst)

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Abstract

A series of twenty S-benzyl ortho-aminothiophenol and S,S′-xylylene-bridged bis(ortho-aminothiophenol) compounds and their imine derivatives have been synthesized in moderate to excellent yields and characterized. The syntheses were optimized, including large-scale syntheses, and an improved purification method involving the HCl salt was developed. This paper also serves as a comprehensive review of xylylene-bridged bis(ortho-amino­thiophenol) compounds.

Key words

Schiff bases - sulfur - nitrogen - ligands - alkylation