A NEW SYNTHETIC ROUTE TO α-ARYL PROPIONIC ACID AND A QUANTITA-TIVE STUDY OF THE PHOTO-S_(RN)1 REAC-TION OF ARYL HALIDES WITH CAN-BANION FROM ALKYL NITRILE

摘要

A new synthetic route leading to α-(2-(6-methoxynaphthy1))-propionic acid has ben developed. Successive one-step preparation of the appropriate α-aryl propionitrile from the aryl halides with propionitrile by photo-SRN1 procedure followed by hydrolysis gives the desired α-aryl propionic acid in excellent total yield. The photostimulated reaction of 2-bromonaph-thalene with acetonitrile or propionitrile in KNH2-NH3 solution to form the corresponding nucleophilic substitution product occurs with quantum yields considerably in excess of unit, while the pseudo-first-order rate constants of the photo-SRN1 are 30.9 and 47.0×10-5mol·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 φ200 and φ313 as well as MO calculation.