63757-55-1Relevant academic research and scientific papers
Neutral sulfur nucleophiles: Synthesis of thioethers and thioesters by substitution reactions of N-heterocyclic carbene boryl sulfides and thioamides
Pan, Xiangcheng,Curran, Dennis P.
supporting information, p. 2728 - 2731 (2014/06/09)
Newly discovered boryl sulfides and N-borylthioamides are shown to serve as neutral sources of sulfur nucleophiles in substitutions reactions. For example, heating of diMe-Imd-BH(SPh)2 with benzyl bromides, primary bromides, or acid chlorides provides the corresponding thioethers or thioesters in high yields. Likewise, N-phenyltetrazole thioethers/esters are made from a readily available N-borylthionotetrazole. The formation of the boryl sulfide and its onward nucleophilic substitution can be telescoped down to a one-pot reaction whose components are an NHC-borane (NHC-BH3), a disulfide, and an electrophile.
Reactivity of di(azido)bis(phosphine) complexes of Ni(II), Pd(II) and Pt(II) toward organic isothiocyanates: Synthesis, structures, and properties of bis(tetrazole-thiolato) and bis(isothiocyanato) complexes
Kim, Yong-Joo,Han, Jin-Taek,Kang, Seok,Han, Won Seok,Lee, Soon W.
, p. 3357 - 3364 (2007/10/03)
Di(azido)bis(phosphine) complexes of Group 10 metals {M(N3)2(PR3)2} underwent substitution with trimethylsilyl isothiocyanate (Me3Si-NCS) to give the corresponding bis(isothiocyanato) complexes, M(NCS)2L2 (M = Pd, L = PMe3 (1), PEt3 (2), PMe2Ph (3); M = Ni, L = PMe3 (4); M = Pt, L = PEt3 (5)), in which the isothiocyanato ligand is N-bound to the metal. By contrast, the bis(azido) complexes of Pd(II) and Pt(II) underwent 1,3-cycloaddition with organic isothiocyanates (R-NCS) to give tetrazole-containing thiolato complexes, M{S[CN4(R)]}2L2 (M = Pd, L = PMe3, R = allyl (6), benzyl (7), ethyl (8), phenyl (9), 2,6-dimethylphenyl (10); L = PMe2Ph, R = phenyl (11); L = PEt3, R = 2,6-dimethylphenyl (12); M = Pt, L = PMe3, R = Ph (13), Et (14); L = PEt3, R = Ph (15)). The chelating phosphine analogues, M{S[CN4(R)]}2L2 (L-L = depe (1,2-bis(diethylphosphino)ethane): R = Ph, M = Pd (16), Pt (17); R = 2,6-dimethylphenyl, M = Pt (18)) could also be obtained. Molecular structures of 6, 9, 14 and 18 clearly show the S-coordination of the thiolato ligands in these complexes. Treatments of tetrazole-thiolate complexes with benzoyl halide derivatives afforded various organic sulfides.
Novel reactions of S,S'-bis(1-phenyl-1H-tetrazol-5-yl) dithiocarbonate
Takeda, Kazuyoshi,Tsuboyama, Kanoko,Takayanagi, Hiroaki,Shirokami, Rie,Takeura, Masumi,Ogura, Haruo
, p. 2334 - 2337 (2007/10/02)
S,S'-Bis(1-phenyl-1H-5-yl) dithiocarbonate (1) was synthesized in good yield from 1-phenyl-5-mercapto-5H-tetrazole (2) and trichloromethyl chloroformate (TCF).The structure of 1 was confirmed by using X-ray crystal analysis.The reagent (1) could be applied to the formation of amides, Friedel-Crafts type reactions, isothiocyanate syntheses, and carbonyl group insertion reactions.Keywords - S,S'-bis(1-phenyl-1H-tetrazol-5-yl) dithiocarbonate; X-ray crystal analysis; amide; isothiocyanate; Friedel-Crafts reaction; carbonyl group insertion reaction.
