REWIEW ARTICLE Org. Commun . 2:4 (2009) 84-119 Utility of cyclohexanethiols in organic synthesis Mohamed A. Metwally *1 and Bakr F. Abdel-Wahab 2 1Department of Chemistry, Faculty of Science, University of Mansoura, P.O. Box 23, Mansoura, Egypt 2Applied Organic Chemistry Department, National Research Center, Dokki, Giza, Egypt (Received June 28, 2008; Revised November 7, 2009; Accepted November 27, 2009) Abstract: Publications on the preparations of cyclohexanethiols and its reactions are reviewed for the first time. Keywords : Cyclohexanethiols; disulphides; displacement reactions CONTENT General information 1. Synthesis 1.1. Synthesis of cyclohexanethiol 1.1.1. From cyclohexene 1.1.2. From cyclohexanol 1.1.3. From 1,2-epithiocyclohexane 1.1.4. From cyclohexyl halide 1.1.5. By photolysis 1.1.6. By hydrolysis of cyclohexyl thiolacetate 1.1.7. By decomposition of 2-(cyclohexylthio)acrylic acid 1.1.8. From silyl protected thiol 1.2. Synthesis of O-substituted cyclohexanethiols 2. Application of cyclohexathiols in organic synthesis 2.1. Oxidation to disulphides 2.2. Oxidation to sulfonic acid 2.3. Oxidation to thiosulfonate 2.4. Coupling with aryl halides 2.5. Reaction with alcohols, amines, carboxylic acids, and ester 2.6. Displacement of SH group 2.7. Addition to unsaturated compounds 2.8. Different Reactions * Corresponding author: E-mail:
[email protected] The article was published by Academy of Chemistry of Globe Publications www.acgpubs.org/OC/index.htm © Published 11/30/2009 EISSN:1307-6175 85 Metwally and Abdel-Wahab ., Org. Commun . (2009) 2:4 84-119 General information Cyclohexanethiol commonly named cyclohexyl mercaptan used as starting material for manufacture of biologically active compounds such as inhibitors of prostaglandin and leukotriene; canine COX-2 inhibitors; phosphodiesterase inhibitors, …etc.