Theoretical Investigation on Rearrangement Mechanism of 2-(2-Methylallyl)-3-(3-methylbuta-1,2-dienyl) Cyclohex-2-enone

Chem. J. Chinese Universities

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Theoretical Investigation on Rearrangement Mechanism of 2-(2-Methylallyl)-3-(3-methylbuta-1,2-dienyl) Cyclohex-2-enone

ZHU Yuan-Qiang¹, GUO Yong¹, XIE Dai-Qian²*

1. College of Chemistry, Sichuan University, Chengdu 610064, China;
2. Institute of Theoretical and Computational Chemistry, School of Chemistry and Chemical Engineering, Nanjing University, Nanjing 210093, China

Received:2006-12-05 Revised:1900-01-01 Online:2008-02-10 Published:2008-02-10
Contact: XIE Dai-Qian

Abstract

Abstract: The sequential rearrangement mechanism from the 2-(2-methylallyl)-3-(3-methylbuta-1,2-dienyl)cyclohex-2-enone to form eight-ring membered compounds was studied at the B3LYP/6-31G(d,p) level. Two pathways were considered. The first pathway includes five processes while the second pathway undergoes only two processes. Both the two pathways have the same rate determining step of the [1,5]-hydrogen migration. In addition, the effect of toluene solvent was assessed by the polarizable continuum model. The calculation results indicate that the second pathway is favorable both in the gas phase and in toluene solvent.

Key words: Reaction mechanism, Density functional theoretical method, [1,5]-Hydrogen migration, Solvent effect, Thermal [2+2]cycloaddition

CLC Number:

O641

TrendMD:

ZHU Yuan-Qiang¹, GUO Yong¹, XIE Dai-Qian²*. Theoretical Investigation on Rearrangement Mechanism of 2-(2-Methylallyl)-3-(3-methylbuta-1,2-dienyl) Cyclohex-2-enone[J]. Chem. J. Chinese Universities, doi: .

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Theoretical Investigation on Rearrangement Mechanism of 2-(2-Methylallyl)-3-(3-methylbuta-1,2-dienyl) Cyclohex-2-enone

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