Theoretical Study on the Reaction Selectivity of the Catalytic Hydrogenation of 3-Analinomethylidene-5,6-2H-dihydropyran-2,4-diones

Chem. J. Chinese Universities ›› 2002, Vol. 23 ›› Issue (6): 1056.

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Theoretical Study on the Reaction Selectivity of the Catalytic Hydrogenation of 3-Analinomethylidene-5,6-2H-dihydropyran-2,4-diones

FANG Ya-Yin^1,2, SHEN Rong-Xin², SUN Hong-Wei², YUAN Man-Xue², LIU Jie^2,3, LI Zheng-Ming^2,3, LAI Cheng-Ming^2,3

1. Department of Chemistry, Xuzhou Normal University, Xuzhou 221009, China;
2. Department of Chemistry, Nankai University, Tianjin 300071, China;
3. State Key Laboratory of Elemento-Organic Chemistry, Nankai University, Tianjin 300071, China

Received:2001-02-19 Online:2002-06-24 Published:2002-06-24

Abstract

Abstract: Based on diverse groups(R), which located on the 6-substituted site of the dihydropyrandione ring, the final products obtained from the catalytic hydrogenation of 3-analinomethylidene-5,6-2H-dihydropyran-2,4-diones are very different. The selectivity of the title reaction has been studied by means of B3LYP/6-311G^**, AM1 semi-empirical method and molecular mechanics (Tripos force field). The results obtained show that the reaction selectivity is decided by the stability of radical intermediate at the first step and the stability is affected by group R.

Key words: Reaction selectivity, Catalytic hydrogenation, Dihydropyrandione, DFT, AM1

CLC Number:

O641

TrendMD:

FANG Ya-Yin, SHEN Rong-Xin, SUN Hong-Wei, YUAN Man-Xue, LIU Jie, LI Zheng-Ming, LAI Cheng-Ming. Theoretical Study on the Reaction Selectivity of the Catalytic Hydrogenation of 3-Analinomethylidene-5,6-2H-dihydropyran-2,4-diones[J]. Chem. J. Chinese Universities, 2002, 23(6): 1056.

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Theoretical Study on the Reaction Selectivity of the Catalytic Hydrogenation of 3-Analinomethylidene-5,6-2H-dihydropyran-2,4-diones

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