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Synthesis 2008(5): 777-787  
DOI: 10.1055/s-2008-1032186
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© Georg Thieme Verlag Stuttgart · New York

Reactions of p-Benzoquinone with Sulfur Nucleophiles

Alan R. Katritzky*a, Dmytro Fedoseyenkoa, Prabhu P. Mohapatraa, Peter J. Steelb
a Center for Heterocyclic Compounds, Department of Chemistry, University of Florida, Gainesville, FL 32611-7200, USA
b Chemistry Department, University of Canterbury, Christchurch 8140, New Zealand
Fax: +1(352)3929199; e-Mail: katritzky@chem.ufl.edu;
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Publication History

Received 20 July 2007
Publication Date:
18 February 2008 (online)

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Corrected by:

Reactions of p-Benzoquinone with Sulfur NucleophilesSynthesis 2012; 44(21): 3400-3400
DOI: 10.1055/s-0032-1316795

Abstract

The orientations of the reactions of p-benzoquinone with nucleophiles are discussed. The one-pot reaction of p-benzoquinone with alkanethiols gave the 2-, 2,6-, and 2,5-conjugate addition products. Novel 2,6- and 2,5-bis(alkylsulfanyl)-, 2,3,5-tris(alkylsulfanyl)-, and 2,3,5,6-tetrakis(alkylsulfanyl)-p-benzoquinones, and their corresponding hydroquinones, were obtained in good yields through a sequential addition/in situ oxidation protocol for further testing as polymerization inhibitors in rubber and petroleum products. The structures of five 2,5- and 2,6-disubstituted isomers were established by X-ray crystallography.

Key words

p-benzoquinone - thiols - conjugate additions - hydroquinones - polymerization inhibitors

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These data can be obtained free of charge from the Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif.