Density Functional Study on [3+2]-Dipolar Cycloaddition Reaction of the N-heterocyclic Carbene Boryl Azide with Olefins

作者：Zhang Xing hui^*; Wang Ke tai; Niu Teng; Li Shan shan

来源：Bulletin of the Korean Chemical Society, 2014, 35(5): 1403-1408.

DOI：10.5012/bkcs.2014.35.5.1403

• Cycloaddition reaction
• Boryl azide
• Olefin
• Density functional study

The cycloaddition reactions of the N-heterocyclic carbene boryl azide with methyl acrylate, butenone, and hexafluoropropene have been investigated theoretically. Solvent effects on these reactions have been explored by calculation that included a polarizable continuum model (PCM) for the solvent (C6H6). The title reaction could produce 4- and 5-substituted 1,2,3-triazolines, respectively. The reaction systems have the higher chemical reactivity with the low barriers and could be favored. Yet the smaller differences have been found to occur in energetics, and the cycloaddition reactions occur for s-trans conformations over s-cis conformations. The calculations indicated that the cycloaddition reaction of the alkenes have certain regioselectivity.

• 出版日期2014-5-20
• 单位兰州大学