ISSN print edition: 0366-6352 ISSN electronic edition: 1336-9075 Registr. No.: MK SR 9/7 Published monthly

Direct sulfenylation of acetone with benzothiazolesulfenamides to benzothiazolylthio-substituted alkylaminopropene: synthesis and application

Magdaléna Štolcová, Alexander Kaszonyi, Milan Hronec, Tibor Liptaj, and Gabriela Kyselá

Department of Organic Technology, Slovak University of Technology, Radlinského 9, 81237 Bratislava, Slovakia

E-mail: magdalena.stolcova@stuba.sk

Received: 18 February 2009  Revised: 3 July 2009  Accepted: 17 July 2009

Abstract: N-Substituted derivatives of 2-benzothiazolesulfenamides give high yields of 1-(2′-benzothiazolylthio)-2-alkylaminoprop-1-ene and 1,1-bis-(2′-benzothiazolylthio)-2-alkylaminoprop-1-ene in a reaction with acetone in the temperature range from 56°C to 70°C and in the presence of a small amount of water. The α-sulfenylated carbonyl product, 2′-benzothiazolylthiopropan-2-one, is supposed to be an intermediate of this one-pot synthesis. 1,1-Bis-(2′-benzothiazolylthio)-2-tert-butylaminoprop-1-ene has been proved an accelerator of sulfur curing of rubber composites with high processing safety.

Keywords: sulfenamide derivatives - acetone - direct sulfenylation - accelerator of sulfur curing

Full paper is available at www.springerlink.com.

DOI: 10.2478/s11696-009-0085-8

Chemical Papers 64 (1) 65–71 (2010)