Theoretical Study of the Diels-Alder Reactions of Lewis Base-Stabilized Borabenzenes with Dienophiles

Chem. J. Chinese Universities

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Theoretical Study of the Diels-Alder Reactions of Lewis Base-Stabilized Borabenzenes with Dienophiles

WANG Yan^1,2, FANG De-Cai¹*, LIU Ruo-Zhuang¹

1. College of Chemistry, Beijing Normal University, Beijing 100875, China;
2. College of Chemistry and Chemical Engineering, Xinyang Normal University, Xinyang 464000, China

Received:2007-07-11 Revised:1900-01-01 Online:2008-05-10 Published:2008-05-10
Contact: FANG De-Cai

Abstract

Abstract: Density functional theory(DFT) calculations at the B3LYP/6-31G(d) level of theory were employed to study the mechanism and the potential energy surface of Diels-Alder reactions between Lewis base stabilized borabenzene and dienophiles. The solvent effect and substituent effect were also considered. The results indicate that some of the reactions take place in a simple concerted way, while other reactions will form an intermolecular complex first and then proceed through a concerted transition state to obtain final products. The studies on the solvent and substituent effects reveal that the CH₂Cl₂ solvent will elevate the activation barriers, while CO₂Me or CN groups on C atom of acetylene or ethylene may lower the activation barriers considerably. The Diels-Alder reactions forming one C—B bond and one C—C bond are always more favorable than the corresponding Diels-Alder reactions forming two C—C bonds, both thermodynamically and kinetically, which is in agreement with experimental observation.

Key words: Borabenzene, Diels-Alder reaction, Reaction mechanism, Density functional theory

CLC Number:

O641

TrendMD:

WANG Yan^1,2, FANG De-Cai¹*, LIU Ruo-Zhuang¹. Theoretical Study of the Diels-Alder Reactions of Lewis Base-Stabilized Borabenzenes with Dienophiles[J]. Chem. J. Chinese Universities, doi: .

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Theoretical Study of the Diels-Alder Reactions of Lewis Base-Stabilized Borabenzenes with Dienophiles

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