Synthesis and reactions of C-phosphanylated thiazol-2-thiones

The facile regioselective synthesis of the P(iii) substituted thiazol-2-thione 2 is presented. Reaction of 2 with hydrogenperoxide-urea, elemental sulfur and selenium resulted in P(v) chalcogenide thiazol-2-thiones 3-5. All compounds were characterized using (31)P, (1)H, (13)C NMR, IR and elemental...

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Published inDalton transactions : an international journal of inorganic chemistry Vol. 45; no. 7; pp. 2955 - 2962
Main Authors Begum, I, Schnakenburg, G, Streubel, R
Format Journal Article
LanguageEnglish
Published England 21.02.2016
Subjects
Chalcogenides
Chlorides
Desulfurizing
Diffraction
Dimers
NMR spectroscopy
Spectrometry
X-rays
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Summary:The facile regioselective synthesis of the P(iii) substituted thiazol-2-thione 2 is presented. Reaction of 2 with hydrogenperoxide-urea, elemental sulfur and selenium resulted in P(v) chalcogenide thiazol-2-thiones 3-5. All compounds were characterized using (31)P, (1)H, (13)C NMR, IR and elemental analyses and, additionally, by the single-crystal X-ray diffraction technique. Oxidative desulfurization of the 5-phosphinoylated thiazol-2-thione 3 using hydrogenperoxide led to the first C-phosphanoyl substituted thiazolium salt (6). Deprotonation of 6 and in situ reaction with the cyclooctadiene rhodium(i) chloride dimer yielded thiazol-2-ylidene rhodium(i) complex 7 which was confirmed by NMR spectroscopy and ESI-MS spectrometry.
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ISSN:1477-9226
1477-9234
DOI:10.1039/c5dt03662c