A new synthetic route to alpha aryl propionic acid and a quantitative study of the photo s r n1 reaction of aryl halides with carbanion from alkyl nitrile
Wu B Q.; Zeng F W.; Ge M J.; Cheng X Z.; Wu G S.
Science in China Series B Chemistry Life Sciences and Earth Sciences 34(7): 777-786
A new synthetic route leading to .alpha.(2-(6-methoxynaphthyl))-propionic acid has been developed. Successive one-step preparation of the appropriate .alpha.-aryl propionitrile from the aryl halides with propionitrile by photo-SRN1 procedure followed by hydrolysis gives the desired .alpha.-aryl propionic acid in excellent total yield. The photostimulated reaction of 2-bromonaphthalene with acetonitrile or propionitrile in KNH2-NH3 solution to form the corresponding nucleophilic substitution products occurs with quantum yields considerably in excess of unit, while the pseudo-first-order rate constants of the photo-SRN1 are 30.9 and 47.0 .times. 10-5 mol .cntdot. s-1, respectively. Definite evidence to support the excitation of ground CTC and electron transfer from anion to ArX within the complex comes from the observation of the same .vphi.>200 and .vphi.>313 as well as MO calculation.