bis(methylsulfanyl)methanethione

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:90.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Dimethyl sulfate (22.84 mL, 240 mmol) and dimethyl trithiocarbonate (26.48 mL, 240 mmol) were added to acetonitrile (80 mL). The resultant dark yellow solution was heated to 90° C. for 2 hours. The mixture was then allowed to cool to 55° C. and then a solution of tetrafluoroboric acid (54% in diethyl ether, 48 mL) was added over 5 min time. The resultant solution was stirred for an additional 15 min, followed by pouring it into a solution of ice-cold diethyl ether (600 mL). The white solid that formed was collected and washed with diethyl ether (3×50 mL) and dried in a vacuum oven to provide (bis-methylsulfanyl-methylene)-methyl-sulfonium tetrafluoroborate salt (47.3 g, 83%) as a colorless solid. to cool to 55° C. The white solid that formed was collected washed with diethyl ether (3×50 mL) dried in a vacuum oven

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Sodium tert-butoxide (1.24 g, 12.9 mmol) was added portionwise over 2 min to a solution of 2,7-dibromofluorene (2.0 g, 6.2 mmol) in DMSO (40 ml) at RT under nitrogen. To the resulting red solution was added dimethyl trithiocarbonate (0.94 g, 6.8 mmol) via a syringe. The reaction was stirred for 5 min and methyl iodide (1.8 g, 12.6 mmol) was added over 2 min. The reaction was stirred for 1 h worked up as above. Recrystallization from ethyl acetate/THF (2:1) afforded 2.4 g (91%). The sample was identical in all respects to that described above. The reaction was stirred for 1 h Recrystallization from ethyl acetate/THF (2:1) afforded 2.4 g (91%)

反応条件: temp:90.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Dimethyl trithiocarbonate (2.76 g, 20 mmol) was treated with dimethyl sulfate (2.5 g, 20 mmol) and stirred at 90° C. for 1 h, and cooled to 25° C. The solid was broken up under ether, collected by filtration, and washed with ether to give the title compound (5.1 g, 91%). cooled to 25° C collected by filtration washed with ether

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a mixture of NaH (240 mg, 6.0 mmol, 60% in mineral oil) and 1-cyclopropylethanone (168.2 mg, 2.0 mmol) in DMF (1 mL) was added dimethyl carbonotrithioate (304.3 mg, 2.2 mmol) at rt. The reaction was quenched with water after 3 h and extracted with EtOAc. The organic layer was washed with brine, dried over Na2SO4, filtered and concentrated to yield crude 1-cyclopropyl-3,3-bis(methylthio)prop-2-en-1-one 30 which was purified by flash chromatography on silica with 15% EtOAc in hexanes as eluant. 1H NMR (400 MHz, CDCl3) δ 6.14 (s, 1H), 2.41 (s, 3H), 2.40 (s, 3H), 1.81 (m, 1H), 1.00 (m, 2H), 0.77 (m, 2H). MS m/z 189.0 (M+1). The reaction was quenched with water after 3 h extracted with EtOAc The organic layer was washed with brine dried over Na2SO4 filtered concentrated

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a stirred solution of phenylhydrazine (30 mmol, 1 equiv) in dry acetonitrile (20 mL) was added trithiocarbonic acid dimethyl ester (30 mmol, 1 equiv) slowly at ice bath temperature. The mixture was stirred for 18 hours and diluted with diethylether (30 mL). The resulting white solid was filtered and was washed with ether and dried under nitrogen to afford title compound. The resulting white solid was filtered was washed with ether dried under nitrogen