Solid and Solution Phase Organic Syntheses of Oligomeric Thioureas

• Published in: Journal of organic chemistry Vol. 61; no. 25; pp. 8811 - 8818
• Main Authors: Smith, Joseph, Liras, Jennifer L, Schneider, Stephen E, Anslyn, Eric V
• Format: Journal Article
• Language: English
• Published: United States American Chemical Society 13-12-1996
• ISSN: 0022-3263; 1520-6904
• DOI: 10.1021/jo9614102

In order to study supramolecular architectures built from unnatural oligomeric and polymeric structures, one must first have an efficient synthetic strategy to produce them. Oligomers built from thiourea groups should form complex secondary and tertiary structures due to the hydrogen-bonding capabilities of the thioureas. Herein, both solution and solid phase synthetic procedures that yield oligomeric thioureas are described. They rely on the coupling of an isothiocyanate with an amine to produce the thiourea linkage. The monomers are derived from simple diamines. Higher yields are achieved using the solid phase method due to the ability to easily monitor the extent of reaction, to use a large excess of reagent, and to perform purification after cleavage from the solid support. A variety of oligomers are given as examples. The procedure is quite general, should be easily extended to complex monomers, and will allow the investigation of intramolecular and intermolecular interactions.