Issue 18, 2003
From the journal:

Organic & Biomolecular Chemistry

Reappraising the formation of Jaffé's base: studies of the treatment of imidazolidine-2-thione with mild oxidising agents

Yupa Thanyasirikul,ab   Chaveng Pakawatchai,ab   Marcus L. Cole,c   Peter C. Junk,*bc   Brian W. Skeltonb  and  Allan H. Whiteb  

* Corresponding authors

a Department of Chemistry, Prince of Songkla University, Hat Yai, Thailand 90112

b Chemistry, The University of Western Australia, Crawley, W. A. 6009, Australia

c School of Chemistry, Monash University, Victoria 3800, Australia
E-mail: Peter.Junk@sci.monash.edu.au
Fax: +61 (0)3 9905 4570
Tel: +61 (0)3 9905 4597

Abstract

Throughout reports detailing the preparation of Jaffé's Base, which date as far back as 1894, its identity and the nature of an intermediate prior to its formation have been constant points of conjecture. This report presents firm evidence that the oxidation of imidazolidine-2-thione, SCN(H)C2H4N(H), with potassium triiodide yields the ‘thiol’ condensation product 2,2′-bis(4,5-dihydro-1H-imidazolidine)disulfide {NC2H4N(H)CS}2 (1), which under mild conditions undergoes partial self condensation to yield 1-(4,5-dihydro-1H-imidazolidin-2-yl)imidazolidine-2-thione, Jaffé's Base – SCN(CNC2H4N(H))C2H4NH, (2). Crystallisation of 1 from acetone results in the unexpected formation of heterobicyclic 3-methyl-5,6-dihydroimidazolidin[2,1-b]thiazole, 3. The conversion of 1 to 3 has been studied by 1H NMR spectroscopy, which suggests the concurrent formation of 2 as an unreactive by-product. The solid state structures of 2, its HBr salt (2·HBr) and 3·(HI·I2), the latter being the isolated form of 3 under the conditions employed, have been determined using XRD methods.

Graphical abstract: Reappraising the formation of Jaffé's base: studies of the treatment of imidazolidine-2-thione with mild oxidising agents

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Article information

DOI
https://doi.org/10.1039/B306647A
Article type
Paper
Submitted
13 Jun 2003
Accepted
31 Jul 2003
First published
19 Aug 2003

Org. Biomol. Chem., 2003,1, 3217-3222

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Reappraising the formation of Jaffé's base: studies of the treatment of imidazolidine-2-thione with mild oxidising agents

Y. Thanyasirikul, C. Pakawatchai, M. L. Cole, P. C. Junk, B. W. Skelton and A. H. White, Org. Biomol. Chem., 2003, 1, 3217 DOI: 10.1039/B306647A

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