Issue 47, 2016
From the journal:

Organic & Biomolecular Chemistry

Atropisomerism in 3-arylthiazolidine-2-thiones. A combined dynamic NMR and dynamic HPLC study†

A. Ciogli,*a   S. Vivek Kumar,b   M. Mancinelli,c   A. Mazzanti, ORCID logo *c   S. Perumal,*b   C. Severi ORCID logo c  and  C. Villani ORCID logo a  

* Corresponding authors

a Department of Chemistry and Technologies of Drug, Sapienza University of Rome, Piazzale A. Moro 5, I-00185 Rome, Italy

b Department of Organic Chemistry, School of Chemistry, Madurai Kamaraj University, Madurai-625021, Tamil Nadu, India

c Department of Industrial Chemistry “Toso Montanari”, University of Bologna, Viale Risorgimento 4, I-40136 Bologna, Italy
E-mail: andrea.mazzanti@unibo.it

Abstract

Sterically hindered 3-arylthiazolidine-2-thiones were prepared by a solvent-free reaction with arylisothiocyanates and 1,4-dithiane-2,5-diol. Atropisomerism was observed in two compounds (3 and 4, aryl = 1-naphthyl and 2-methylnaphth-1-yl), whose rotational energy barriers were measured using dynamic NMR and dynamic HPLC. The experimental analyses were supported by DFT calculations. Thermally stable atropisomers were obtained by dehydration of compounds 3 and 4 and the absolute configuration of the atropisomers of compound 6 was determined by theoretical simulation of the ECD and VCD spectra.

Graphical abstract: Atropisomerism in 3-arylthiazolidine-2-thiones. A combined dynamic NMR and dynamic HPLC study

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Article information

DOI
https://doi.org/10.1039/C6OB02145J
Article type
Paper
Submitted
03 Oct 2016
Accepted
31 Oct 2016
First published
31 Oct 2016

Org. Biomol. Chem., 2016,14, 11137-11147

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Atropisomerism in 3-arylthiazolidine-2-thiones. A combined dynamic NMR and dynamic HPLC study

A. Ciogli, S. Vivek Kumar, M. Mancinelli, A. Mazzanti, S. Perumal, C. Severi and C. Villani, Org. Biomol. Chem., 2016, 14, 11137 DOI: 10.1039/C6OB02145J

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