| 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 |
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| 引用本文： | 吴碧琪,曾繁文,葛明娟,程新中,吴国生.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[J].中国科学B辑(英文版),1991(7). |
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| 作者姓名： | 吴碧琪 曾繁文 葛明娟 程新中 吴国生 |
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| 作者单位： | Shanghai Institute of Organic Chemistry，Academia Sinica，Shanghai 200032，PRC，Shanghai Institute of Organic Chemistry，Academia Sinica，Shanghai 200032，PRC，Shanghai Institute of Organic Chemistry，Academia Sinica，Shanghai 200032，PRC，Shanghai Institute of Organic Chemistry，Academia Sinica，Shanghai 200032，PRC，Shanghai Institute of Organic Chemistry，Academia Sinica，Shanghai 200032，PRC |
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| 基金项目： | Project supported by the National Natural science Foundation of China |
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| 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 φ>200 and φ>313 as well as MO calculation.
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| 关 键 词： | α-aryl propionie acid group CTC MO calculation. |
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