(E)-3-(phenylsulfonyl)acrylonitrile

(E)-3-(phenylsulfonyl)acrylonitrile :

CAS No.	64326-47-2
Chemical Name:	(E)-3-(phenylsulfonyl)acrylonitrile
Synonyms:	(E)-3-(phenylsulfonyl)acrylonitrile
Molecular Formula:	C9H7NO2S
Formula Weight:	193

2,3-dibromopropanenitrile (1.07 g, 5 mmol) was added to a solution of sodium benzensulfinate (820 mg, 5 mmol) in H2O:dioxane (15+15 mL), followed by CH3COOH (286 L, 5 mmol) and CH3COONa (411 mg, 5 mmol). The reaction mixture was stirred for 21 h at room temperature, then concentrated to half volume, and poured into sat. solution of NaHCO3 (15 mL) and extracted with CH2Cl2 (3 x 20 mL). Combined organic extracts were dried over MgSO4, filtered, and the residual brown oil was purified by flash column chromatography (SiO2, hexane/EtOAc 3:2) to afford E isomer (714 mg, 74%, white solid) and Z isomer (173 mg 18%, white solid).

E isomer:

1 H NMR (300 MHz, CDCl3): δ = 7.94-7.91 (m, 2H), 7.78- 7.73 (m, 1H), 7.67-7.62 (m, 1H), 7.28 (d, J = 15.7 Hz, 1H), 6.57 (d, J = 15.7 Hz, 1H) ppm.

13C NMR (75 MHz, CDCl3): δ = 149.18, 137.41, 135.16, 130.06, 128.62, 113.50, 110.84 ppm.

Z isomer:

1 H NMR (300 MHz, CDCl3): 8.00 (m, 1H), 7.75-7.70 (m, 1H), 7.63-7.58 (m, 1H), 7.08 (d, J = 11.3 Hz, 1H), 6.04 (d, J = 11.3 Hz) ppm.

13C NMR (75 MHz, CDCl3) δ 148.42, 138.27, 135.29, 130.07, 128.77, 108.85 ppm.

Spectral data for both isomers were identical with those reported in the literature.

Berdnikov, E. A., Mukhitova, F. K., Tantasheva, F. R., Kataev, E. G. Zh. Org. Khim. 1977, 13, 1418. 135.

Bradley, P. J., Grayson, D. H. J. Chem. Soc. Perkin. Trans. 1. 2002, 1794.

/////////