Substance 2p was ready following general treatment GP-A from azirine 1e (150 mg, 0.91 mmol), 4-bromobenzonitrile (14 g, 77 mmol) and Rh2(oct)4 (7 mg, 0.0091 mmol) in DCE (150 mL) in 89 mg (31% produce, following column chromatography in silica (light petroleum/ethyl acetate, 9:1C8:1 (1.39 (s, 9H), 3.00 (s, 1H), 7.04 (s, 1H), 7.55C7.57 (m, 2H), 7.78-7.80 (m, 2H). DCE (150 mL) in 135 mg (49% produce, after column chromatography on Ly93 silica (light petroleum/ethyl acetate, 7:1C4:1 (2.36 (s, 3H), 3.27 (s, 1H), 6.85 (s, 1H), 7.73C7.79 (m, 4H). 13C1H-NMR (CDCl3, 100 MHz): 13.9 (CH3), 25.3 (CH), 122.6 (C), 124.5 (CH), 128.6 (C), 131.1 (CH), 132.8 (CH), 150.7 (C), 160.9 (C), 162.1 (C). HRMS (ESI) (2c). Substance 2c was ready following general treatment GP-A from azirine 1c (100 mg, 0.41 mmol), acetonitrile (4.3 mL, 82 mmol) and Rh2(oct)4 (3 mg, 0.0041 mmol) in DCE (100 mL) in 63 mg (61% produce, following column chromatography in silica (light petroleum/ethyl acetate, 10:1 (1.77C1.85 (m, 6H), 1.95C1.98 (m, 6H), 2.10C2.13 (m, 3H), 2.38 (s, 3H), 2.81 (s, 1H), 6.75 (s, 1H). 13C1H-NMR (CDCl3, 100 MHz): 13.9 (CH3), 24.0 (CH), 27.5 (CH), 35.6 (C), 36.4 (CH2), 38.2 (CH2), 123.6 (CH), 152.0 (C), 160.2 (C), 170.7 (C). HRMS (ESI) (2d). Substance 2d was ready following general treatment GP-A from azirine 1a (185 mg, 1 mmol), propionitrile (14.3 mL, 200 mmol) and Rh2(oct)4 (8 mg, 0.01 mmol) in DCE (200 mL) in 121 mg (57% produce, following column chromatography in silica (light petroleum/ethyl acetate, 11:1C7:1 (1.26 (t, 3H, = 7.6 Hz), 2.69 (q, 2H, = 7.6 Hz), 3.26 (s, 1H), 6.83 (s, 1H), 7.56C7.66 (m, 3H), 7.90C7.93 (m, 2H). 13C1H-NMR (CDCl3, 100 MHz): 11.1 (CH3), 21.7 (CH2), 25.1 (CH), 123.8 (C), 124.1 (CH), 129.3 (C), 129.9 (CH), 133.6 (CH), 151.0 (C), 162.5 (C), 165.2 (C). HRMS (ESI) (2e). Substance 2e was ready following general treatment GP-A from azirine 1d (215 mg, 1 mmol), propionitrile (14.3 mL, 200 mmol) and Rh2(oct)4 (8 mg, 0.01 mmol) in DCE (200 mL) in 117 mg (48% produce, following column chromatography in silica (light petroleum/ethyl acetate, 4:1 (1.26 (t, 3H, = 7.6 Hz), 2.69 (q, 2H, = 7.6 Hz), 3.19 (s, 1H), 3.91 (s, 3H), 6.80 (s, 1H), 7.06C7.09 (m, 2H), 7.84C7.87 (m, 2H). 13C1H-NMR (CDCl3, 100 MHz): 11.0 (CH3), 21.7 (CH2), 24.7 (CH), 55.6 (CH3), 114.9 (CH), 116.1 (C), 123.8 (CH), 131.9 (CH), 151.3 (C), 161.1 (C), 163.8 (C), 165.02 (C). HRMS (ESI) (2f). Substance 2f was ready following general treatment Ly93 GP-A from azirine 1e (150 mg, 0.91 mmol), propionitrile (9.7 mL, 136 mmol) and Rh2(oct)4 (7 mg, 0.0091 mmol) in DCE (150 mL) in 67 mg (38% produce, following column chromatography in silica (light petroleum/ethyl acetate, 6:1 (1.27 (t, 3H, = 7.6 Hz), 1.34 (s, 9H), 2.70 (q, 2H, = 7.6 Hz), 2.90 (s, 1H), 6.80 (s, 1H). 13C1H-NMR (CDCl3, 100 MHz): 11.0 (CH3), 21.6 (CH2), 24.5 (CH), 26.0 (CH3), 33.3 (C), 123.6 (CH), 151.4 (C), 164.7 (C), 171.8 (C). HRMS (ESI) (2g). Substance 2g was ready following general treatment GP-A from Rabbit Polyclonal to CDKA2 azirine 1d (200 mg, 0.76 mmol), benzyl cyanide (12.9 g, 110 mmol) and Rh2(oct)4 (6 mg, 0.0076 mmol) in DCE (200 mL) in 94 mg (35% produce, after column chromatography in silica (toluene/light petroleum/ethyl acetate, 20:1 + 0.5% triethylamine (3.30 (s, 1H), 4.06 (s, 2H), 6.89 (s, 1H), 7.26C7.35 (m, 5H), 7.75C7.81 (m, 4H). 13C1H-NMR (CDCl3, 100 MHz): 25.3 (CH), 34.6 (CH2), 122.6 (C), 124.5 (CH), 127.1 (CH), 128.7 (CH), 128.8 (C), 131.1 (CH), 132.8 (CH), 135.3 (C), 151.3 (C), 161.9 (C), 161.9 (C), 162.5 (C). HRMS (ESI) (2h). Substance 2h Ly93 [27] was ready following general treatment GP-A from azirine 1a (500 mg, 2.7 mmol), benzonitrile (29 mL, 284 mmol) and Rh2(oct)4 (2.1 mg, 0.027 mmol) in DCE (250 mL) in 302 mg (43% produce, after column chromatography in silica (light petroleum/ethyl acetate, (3 7:1.37 (s, 1H), 7.06 (s, 1H), 7.38C7.42 (m, 3H), 7.59C7.67 (m, 3H), 7.92C7.98 (m, 4H). (2i). Substance 2i was ready.