oxepan-2-one

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

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

Procedure: To a 250 mL two necked flask equipped with a condenser containing e-caprolactone (3,3 mL, 30 mmol) and anhydrous tetrahydrofuran (60 mL) under nitrogen atmosphere, was added at 0° C. dropwise propylmagnesium chloride (33 mL, 66 mmol, 2,2 eq., 2.0 M solution in diethyl ether). After addition, the reaction was stirred for 10 minutes at room temperature before heating to reflux for 2 hours. The reaction was monitored by thin layer chromatography. The reaction was cooled to 0° C. and saturated aqueous ammonium chloride (18 mL) was added followed, at room temperature, by hydrochloric acid (18 mL, 1 M aqueous). The organic phase was decanted and the aqueous phase extracted with dichloromethane (3×140 mL). The combined organic phases were washed with saturated aqueous sodium bicarbonate (100 mL) before drying over magnesium sulfate. Evaporation of the solvent gave the title compound (6,543 g, 96%) as a viscous yellow oil. 1H NMR (CDCl3, 400 MHz) d?(ppm): 3,64 (t, J=6,7 Hz, 2H); 1,59 (tt, J=6,7 Hz, J=6,7 Hz, 2H); 1,46-1,24 (m, 15H); 0,88 (t, J=7,2 Hz, 6Hd). 13C NMR (CDCl3, 129,9 MHz) d?(ppm): 68,5; 64,2; 42,0 (2C′); 39,8; 33,1; 26,8; 23,7; 17,1 (2C′); 14,5 (2C′). MS (IC+) m/z (%): 220,2 [M+18] (99); 202,2 (75); 203,3 [M+1] (30); 185,2 (100); 176,2 (60); 141,2 (25). After addition before heating to reflux for 2 hours The reaction was cooled to 0° C. The organic phase was decanted the aqueous phase extracted with dichloromethane (3×140 mL) The combined organic phases were washed with saturated aqueous sodium bicarbonate (100 mL) before drying over magnesium sulfate Evaporation of the solvent

Conditions: temp:180.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: ε-Caprolactone (170 g, 1.49 mole), glycolide (30 g, 0.26 mole), lauryl alcohol (1.37 g, 7.3×10-3 mole) and stannous octoate (0.052 g, 1.2×10-4 mole) were combined in a stirred reactor under nitrogen at 180° C. The mixture was stirred at 180° C. for 4.5 hours. The resulting polymer had an inherent viscosity of 0.68 dl/g (0.5 g/dl in CHCl3). The composition was determined by 1H NMR to be 85 wt. % ε-caprilactone and 15 wt. % glycolide.

Conditions: temp:135.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: ε-Caprolactone (40 g, 0.35 mole), trimethylene carbonate (10 g. 0.098 mole), lauryl alcohol (1.42 g, 7.6×10-3 mole) and stannous chloride dihydrate (10.1 mg, 4.5×10-5 mole) were combined in a flask and heated for 24 hours under nitrogen at 135° C. The resulting polymer had an inherent viscosity of 0.42 dl/g (0.5 g/dl in HFAS). The composition was determined by 1H NMR to be 86 wt. % caprolactone and 14 wt. % trimethylene carbonate.

Conditions: temp:135.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: ε-Caprolactone (8.0 g, 0.070 mole), trimethylene carbonate (2.0 g, 0.020 mole), lauryl alcohol (0.283 g, 1.52×10-3 mole) and stannous chloride dihydrate (2.02 mg, 8.91×10-6 mole) were combined in a flask. The flask was flushed with nitrogen, evacuated and sealed. The flask was heated at 135° C. for 24 hours. The resulting polymer had a composition, as measured by 1H NMR, of 86 wt. % ε-caprolactone and 14 wt. % trimethylene carbonate. The ηinh of the copolymer was 0.26 dl/g (0.5 g/dl in HFAS). The flask was flushed with nitrogen evacuated sealed