Synthesis of 4,5‐Dimethyl‐1,3‐Dithiol‐2‐One

Abstract

O‐ Isopropyl S‐ 3‐Oxobutan‐2‐yl dithicarbonate 2‐Butanone Potassium O‐ isopropylxanthate 4,5‐Dimethyl‐1,3‐dithiol‐2‐one

Redox-Active Metallodithiolene Groups Separated by Insulating Tetraphosphinobenzene Spacers

“…■ EXPERIMENTAL SECTION General Considerations. Literature procedures were employed for the syntheses of 1,2-bis(diphenylphosphino)benzene (dppb), 16 1,2,4,5-tetrakis(diphenylphosphino)benzene (tpbz), 17 disodium 1,2dicyano-ene-1,2-dithiolate (Na 2 (S 2 C 2 (CN) 2 ), Na 2 mnt), 18 4,5-dimethyl-1,3-dithiol-2-one, 19 4,5-bis(4-methoxyphenyl)-1,3-dithiol-2-one, 20 2,2-dimethyl-4,5-dicyano-1,3,2-dithiastannole ([(mnt)SnMe 2 ]), 21 2,2dimethyl-4,5-bis(4-methoxyphenyl)-1,3,2-dithiastannole ([(adt)-SnMe 2 ]), 20 2,2-dimethyl-4,5-dimethyl-1,3,2-dithiastannole ([(mdt)-SnMe 2 ]), 22 2,2-di-n-butyl-4,5-dimethyl-1,3,2-dithiastannole ([(mdt)-Sn n Bu 2 ]), 22 [Cl 2 M(dppb)] (M = Ni, 23 Pd 24 ), [NiCl 2 (dme)] 25 (dme = 1,2-dimethoxyethane), [Cl 2 Pt(μ-tpbz)PtCl 2 ], 26 [M(pdt) 2 ] 27 (pdt = 1,2-diphenyl-1,2-ethylenedithiolate; M = Ni, Pd, Pt), [PdCl 2 (cod)] (cod = 1,5-cyclooctadiene), 28 [(adt)Pd(dppb)], 15 tpbz)Pd(adt)] (18; adt = 1,2-di-p-anisyl-1,2-ethylenedithiolate). 15 All other reagents were purchased from commercial sources and used as received.…”

Organic Molecular Conductors Based on Tetramethyl-TTP: Structural and Electrical Properties Modulated by the Anion Size and Shape

“…Synthesis of TMTTP and Preparation of Radical Cation Salts. The desired TMTTP was not yielded by the reaction conditions of 1,3-dithiol-2-thione fused with dimethyl-TTF (1) 16 and two or four equimolar amounts of 4,5dimethyl-1,3-dithiol-2-one (2) 47,48 in the presence of trimethyl phosphite. When 10 equimolar amounts of 2 were used, the desired TMTTP was obtained in a 5.0% yield, and the yield was improved a little by 5.6 and 9.3% using 20 and 30 equimolar amounts of 2, respectively (Scheme 1 and Table S1).…”

“…Synthesis of TMTTP. To a mixture of 116 (500 mg, 1.48 mmol) and 247,48 (6.47 g, 44.3 mmol) in toluene (35 mL) was added trimethyl phosphite (35 mL), and the solution was stirred at 100 °C for 2 h. The reaction mixture was cooled to room temperature and concentrated under reduced pressure. Methanol was added, and then, the resulting brown precipitate was collected by filtration and washed with methanol.…”