Issue 6, 2013
From the journal:

RSC Advances

Thermal fragmentation of spirodithiohydantoins: A novel route to NHCs†

Davit Jishkariani,a   C. Dennis Hall,a   Alexander Oliferenko,a   Blake J. Tomlin,a   Peter J. Steelb  and  Alan R. Katritzky*ac  

* Corresponding authors

a Center for Heterocyclic Compounds, Department of Chemistry, University of Florida, Gainesville, FL 32611-7200, USA
E-mail: katritzky@chem.ufl.edu
Fax: +1-352-392-9199
Tel: +1-352-392-0554

b University of Canterbury, Christchurch, New Zealand

c Department of Chemistry, King Abdulaziz University, Jeddah, Saudi Arabia

Abstract

Spirodithiohydantoins undergo a two-step thermal fragmentation affording zwitterionic betaine intermediates and N-heterocyclic carbenes (NHCs) respectively. Such reactions are novel, occur under mild conditions and give NHCs in high yield and purity. This phenomenon was studied using various spectroscopic techniques and control experiments with elemental sulfur. Quantum chemical calculations were employed to provide a deeper understanding of such transformations.

Graphical abstract: Thermal fragmentation of spirodithiohydantoins: A novel route to NHCs

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Article information

DOI
https://doi.org/10.1039/C2RA22487A
Article type
Communication
Submitted
11 Oct 2012
Accepted
09 Nov 2012
First published
13 Nov 2012

RSC Adv., 2013,3, 1669-1672

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Thermal fragmentation of spirodithiohydantoins: A novel route to NHCs

D. Jishkariani, C. D. Hall, A. Oliferenko, B. J. Tomlin, P. J. Steel and A. R. Katritzky, RSC Adv., 2013, 3, 1669 DOI: 10.1039/C2RA22487A

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