prop-1-ynylbenzene

Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: In a dry 25 mL Schlenk-tube, which has been flooded with argon, [Mo(≡N)(OSiPh3)3)(bipy)] (109.2 mg, 0.10 mmol), CuCl2 (13.4 mg, 0.10 mmol), and 1-phenyl-1-propine (116.2 mg, 1.00 mmol) were suspended in dry toluene (5 mL). The reaction mixture was stirred for 3 h at 80° C. and was filtered after cooling over a short silica gel column. The filtrate was concentrated and the residue was purified by means of column chromatography (hexane). 76.1 mg of tolane (85%) were isolated as white solid, the spectroscopic and analytical data of which were identical to those of a commercial sample. M.p.=59-61° C. was filtered after cooling over a short silica gel column The filtrate was concentrated the residue was purified by means of column chromatography (hexane)

Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: In a dry 25 mL Schlenk-tube, which has been flooded with argon, [Mo(≡N)(OSiPh3)3)(bipy)] (109.2 mg, 0.10 mmol), MnCl2 (12.6 mg, 0.10 mmol), and 1-phenyl-1-propine (116.2 mg, 1.00 mmol) were suspended in dry toluene (5 mL). The reaction mixture was stirred for 3 h at 80° C. and was filtered after cooling over a short silica gel column. The filtrate was concentrated and the residue was purified by means of column chromatography (hexane). 77.3 mg of tolane (87%) were isolated as white solid, the spectroscopic and analytical data of which were identical with those of a commercial sample. M.p.=59-61° C. was filtered after cooling over a short silica gel column The filtrate was concentrated the residue was purified by means of column chromatography (hexane)

Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: In a dry 25 mL Schlenk-tube, which has been flooded with argon, [Mo(≡N)(OSiPh3)3)(bipy)] (109.2 mg, 0.10 mmol), MnCl2 (12.6 mg, 0.10 mmol), and 1-phenyl-1-propine (116.2 mg, 1.00 mmol) were suspended in dry toluene (5 mL). The reaction mixture was stirred for 3 h at 80° C. and was filtered after cooling over a short silica gel column. The filtrate was concentrated and the residue was purified by means of column chromatography (hexane). 77.3 mg of tolane (87%) were isolated as white solid, the spectroscopic and analytical data of which were identical with those of a commercial sample. M.p.=59-61° C. was filtered after cooling over a short silica gel column The filtrate was concentrated the residue was purified by means of column chromatography (hexane)

Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: In a 25 mL Schlenk-tube, which has been flooded with argon, [Mo(≡N)(OSiPh3)3)(bipy)] (109.2 mg, 0.10 mmol), MnCl2 (12.6 mg, 0.10 mmol), molecular sieve 5 Å (1.0 g) and 1-phenyl-1-propine (116.2 mg, 1.00 mmol) were suspended in dry toluene (5 mL). The reaction mixture was stirred for 3 h at 80° C. and was filtered after cooling over a short silica gel column. The filtrate was concentrated and the residue was purified by means of column chromatography (hexane). 88.0 mg of tolane (98%) were obtained as a white solid, the spectroscopic and analytical data thereof were identical with those of a commercial sample. M.p.=59-61° C. was filtered after cooling over a short silica gel column The filtrate was concentrated the residue was purified by means of column chromatography (hexane)

Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: In a dry 25 mL Schlenk-tube, which has been flooded with argon, [Mo(≡N)(OSiPh3)3)(bipy)] (109.2 mg, 0.10 mmol), MnCl2 (12.6 mg, 0.10 mmol) and molecular sieve 5 Å (1.0 g) was suspended in dry toluene (5 mL) and the mixture was heated to 80° C. After 30 min, 1-phenyl-1-propine (116.2 mg, 1.00 mmol) was added, the reaction mixture was stirred for 3 h at 80° C. and was filtered after cooling over a short silica gel column. The filtrate was concentrated and the residue was purified by means of column chromatography (hexane). 88.2 mg of tolane (99%) were isolated as a white solid, the spectroscopic and analytical data were identical to those of a commercial sample. M.p.=59-61° C. was filtered after cooling over a short silica gel column The filtrate was concentrated the residue was purified by means of column chromatography (hexane)

Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: In a dry 25 mL Schlenk-tube, which has been flooded with argon, [Mo(≡N)(OSiPh3)3)(bipy)] (109.2 mg, 0.10 mmol), MnCl2 (12.6 mg, 0.10 mmol) and molecular sieve 5 Å (1.0 g) was suspended in dry toluene (5 mL) and the mixture was heated to 80° C. After 30 min, 1-phenyl-1-propine (116.2 mg, 1.00 mmol) was added, the reaction mixture was stirred for 3 h at 80° C. and was filtered after cooling over a short silica gel column. The filtrate was concentrated and the residue was purified by means of column chromatography (hexane). 88.2 mg of tolane (99%) were isolated as a white solid, the spectroscopic and analytical data were identical to those of a commercial sample. M.p.=59-61° C. was filtered after cooling over a short silica gel column The filtrate was concentrated the residue was purified by means of column chromatography (hexane)

Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: In a dry 10 mL Schlenk-tube, which has been flooded with argon, [Mo(≡N)(OSiPh3)3(phen)].0.5 toluene (58.8.0 μmol, 68.3 mg) and dried CuCl2 (58.8 μmol, 7.9 mg) were suspended in 2.5 mL of toluene. After addition of 1-phenyl-1-propine (588 μmol, 68.3 mg), the reaction solution was stirred for 24 h at 80° C. and was filtered after cooling over a short silica gel column (2 cm). The filtrate was concentrated and the residue was purified by column chromatography (hexane). 41.0 mg of tolane (78%) were isolated as a white solid, the spectroscopic and analytical data of which were identical to those of a commercial sample. M.p.=59-61° C. was filtered after cooling over a short silica gel column (2 cm) The filtrate was concentrated the residue was purified by column chromatography (hexane)

Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: In a dry 10 mL Schlenk-tube, which has been flooded with argon, [Mo(≡N)(OSiPh3)3(phen)].0.5 toluene (50.0 μmol, 58.1 mg) and MnCl2 (50.0 μmol, 6.3 mg) were suspended in 2.5 mL of toluene. After addition of 1-phenyl-1-propine (500 μmol, 58.1 mg), the reaction solution was stirred for 24 h at 80° C. and was filtered after cooling over a short silica gel column. The filtrate was concentrated and the residue was purified by column chromatography (hexane). 41.6 mg of tolane (93%) were isolated as white solid, the spectroscopic and analytical data of which were identical to those of a commercial sample. M.p.=59-61° C. was filtered after cooling over a short silica gel column The filtrate was concentrated the residue was purified by column chromatography (hexane)

Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: In a dry 10 mL Schlenk-tube, which has been flooded with argon, [Mo(≡N)(OSiPh3)3(phen)].0.5 toluene (50.0 μmol, 58.1 mg) and MnCl2 (50.0 μmol, 6.3 mg) were suspended in 2.5 mL of toluene. After addition of 1-phenyl-1-propine (500 μmol, 58.1 mg), the reaction solution was stirred for 24 h at 80° C. and was filtered after cooling over a short silica gel column. The filtrate was concentrated and the residue was purified by column chromatography (hexane). 41.6 mg of tolane (93%) were isolated as white solid, the spectroscopic and analytical data of which were identical to those of a commercial sample. M.p.=59-61° C. was filtered after cooling over a short silica gel column The filtrate was concentrated the residue was purified by column chromatography (hexane)

Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: In a dry 25 mL Schlenk-tube, which has been flooded with argon, 1-phenyl-1-propine (1.00 mmol, 116.2 mg), [Mo(≡N)(OSiPh3)3(phen)].0.5 toluene (0.100 mmol, 116.2 mg), MnCl2 (0.100 mmol, 12.6 mg) and molecular sieve (1.00 g, 5 Å, powder) were suspended in 5 mL of toluene. The reaction solution was stirred for 3 h at 80° C. and was filtered after the cooling over a silica gel column. The filtrate was concentrated and the residue was purified by column chromatography (hexane). 88.1 mg of tolane (98%) were isolated as a white solid, the spectroscopic and analytical data of which were identical to those of a commercial sample. M.p.=59-61° C. was filtered after the cooling over a silica gel column The filtrate was concentrated the residue was purified by column chromatography (hexane)

Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: In a dry 25 mL Schlenk-tube, which has been flooded with argon, [Mo(≡N)(OSiPh3)3(phen)].0.5 toluene (0.100 mmol, 116.2 mg), MnCl2 (0.100 mmol, 12.6 mg) and molecular sieve (1.00 g, 5 Å, powder) were suspended in 5 mL of toluene and the mixture was heated to 80° C. After 30 min 1-penyl-1-propine (1.00 mmol, 116.2 mg) were added, the reaction mixture was stirred for 3 h at 80° C. and was filtered after cooling over a short silica gel column. The filtrate was concentrated and the residue was purified by column chromatography (hexane). 88.2 mg of tolane (99%) were isolated as white solid, the spectroscopic and analytical data of which were identical to those of a commercial sample. M.p.=59-61° C. was filtered after cooling over a short silica gel column The filtrate was concentrated the residue was purified by column chromatography (hexane)

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a stirred solution of 4.40 mL (40.0 mmol) of phenylpropyne in 30 mL of THF under nitrogen at -75° C. was added a solution of 16 mL (40 mmol) of 2.5M n-butyllithium in hexane over 20 min. The resulting light yellow solution was warmed to 0° C. and stirred for 30 min. This solution was added via syringe to a slurry of 6.25 g (38.0 mmol) of methyl 4-formylbenzoate in 30 mL of THF at -30° C. over 20 min. The resulting light yellow solution was warmed to room temperature and stirred for 30 min. The reaction was quenched with saturated ammonium chloride solution, extracted twice with ether, dried (MgSO4) and evaporated. Purification by flash chromato-graphy (5×15 cm column, 1:19 ether/dichloromethane as elutent) gave title compound as a white solid, mp 48°-50° C., 9.36 g, 88% yield. The resulting light yellow solution was warmed to room temperature stirred for 30 min The reaction was quenched with saturated ammonium chloride solution extracted twice with ether dried (MgSO4) evaporated Purification by flash chromato-graphy (5×15 cm column, 1:19 ether/dichloromethane as elutent)