Uses
trans-4-Methoxy-β-nitrostyrene acts as guest molecule and forms guest molecules forming co-crystal phases with the d-form of robust syndiotactic polystyrene (sPS). It may be employed as a Michael acceptor in the synthesis of proline based chiral ionic liquid catalysts with two five-membered unsaturated aza-heterocycles.
Synthesis
GENERAL STEPS: To a 25 mL sealed tube was added 4-methoxystyrene (0.5 mmol), sodium nitrite (1.5 eq.), potassium persulfate (2.0 eq.), TEMPO (1.2 eq.) and 1,2-dichloroethane (2 mL). The reaction mixture was stirred at 100 °C for 24 hours. After the reaction was completed, it was cooled to room temperature. Extraction was performed by adding dichloromethane (2 mL) and water (5 mL). The organic layer was separated and the aqueous phase was further extracted with dichloromethane (5 mL x 3). The organic layers were combined, dried over anhydrous sodium sulfate and filtered. After the solvent was removed by concentration under reduced pressure, the residue was purified by column chromatography using petroleum ether/ethyl acetate as eluent to give pure 1-methoxy-4-(2-nitrovinyl)benzene.
References
[1] Tetrahedron Letters, 2016, vol. 57, # 1, p. 80 - 84
[2] Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999), 1993, # 12, p. 2399 - 2404
[3] Synlett, 2014, vol. 25, # 14, p. 1997 - 2000
[4] Journal of the American Chemical Society, 2013, vol. 135, # 9, p. 3355 - 3358
[5] Journal of Organic Chemistry, 2013, vol. 78, # 12, p. 5949 - 5954
