Synthesis and reactions of C-phosphanylated thiazol-2-thiones. Issue 7 (11th January 2016)

• Record Type: Journal Article
• Authors: Begum, I.; Schnakenburg, G.; Streubel, R.
• Is Part Of: Dalton transactions. Volume 45:Issue 7(2016)
• Page Start: 2955
• Page End: 2962
• Publication Date: 2016-01-11
• Subjects: Chemistry, Inorganic -- Periodicals; Chemistry, Physical and theoretical -- Periodicals; Chemistry, Inorganic -- Periodicals; 546.05
• DOI: 10.1039/c5dt03662c
• Languages: English
• ISSNs: 1477-9226

Abstract

Abstract : Regioselective synthesis of the P(iii ) substituted thiazole-2-thioneI is presented. Oxidation ofI resulted in P(V) chalcogenide thiazole-2-thiones (E = O, S, Se). Desulfurization ofI (E = O) using hydrogenperoxide led to the first C -phosphanoyl thiazolium saltII . Deprotonation ofII and reaction with cyclooctadiene rhodium(i ) chloride dimer yielded thiazole-2-ylidene rhodium(i ) complexIII . Abstract : The facile regioselective synthesis of the P(iii ) substituted thiazol-2-thione2 is presented. Reaction of2 with hydrogenperoxide–urea, elemental sulfur and selenium resulted in P(v ) chalcogenide thiazol-2-thiones3–5 . 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-thione3 using hydrogenperoxide led to the first C -phosphanoyl substituted thiazolium salt (6 ). Deprotonation of6 and in situ reaction with the cyclooctadiene rhodium(i ) chloride dimer yielded thiazol-2-ylidene rhodium(i ) complex7 which was confirmed by NMR spectroscopy and ESI-MS spectrometry.