Oxidative addition of 3,6-di-tert-butyl-o-benzoquinone and 4,6-di-tert-butyl-N-(2,6-di-iso-propylphenyl)-o-iminobenzoquinone to SnCl2

Addition of 3,6-di-tert-butyl-o-benzoquinone (3,6-DBBQ) to SnCl2 in THF leads to the oxidation of Sn(II) to Sn(IV) with formation of catecholate complex (3,6-DBCat)SnCl2 · 2THF (1), where 3,6-DBCat is 3,6-di-tert-butyl-catecholate dianion. The reaction of 4,6-di-tert-butyl-N-(2,6-di-iso-propylphenyl)-o-iminobenzoquinone (IBQ-Pri) also proceeds on the oxidative-addition mechanism yielding bis-iminosemiquinonato species (ISQ-Pri)2SnCl2(2), where ISQ-Pri is anion-radical 4,6-di-tert-butyl-N-(2,6-di-iso-propylphenyl)-o-iminobenzosemiquinolate. The complexes have been characterized by IR, X-band EPR, 1H NMR (for 1) spectroscopy and magnetochemistry (for 2). X-ray analysis data show the distorted octahedral environment of tin(IV) for both complexes. Complex 1 is diamagnetic (ground state S = 0), while 2 has triplet ground state (S = 1, biradical). Catecholate complex 1 is able to be a spin trap for different organic radicals.

Addition of 3,6-di-tert-butyl-o-benzoquinone or 4,6-di-tert-butyl-N-(2,6-di-iso-propylphenyl)-o-iminobenzoquinone to SnCl2 in THF leads to the oxidation of Sn(II) to Sn(IV) with formation of catecholate (Cat)SnCl2 · 2THF or bis-o-iminobenzosemiquinonato (ISQ)2SnCl2 complexes, respectively. X-ray data show the distorted octahedral environment of tin(IV) for both complexes. The complexes possess a singlet and a triplet ground state correspondingly. Catecholate complex is able to be a spin trap for different organic radicals.Figure optionsDownload as PowerPoint slide