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Studies on the Aromatic Dihalocarbonyl Ylides and Their Deoxygenation
引用本文:Huan Zhenwei,Pan Yinming,Qu Xiaosu and Gao Zhenheng (Department of Chemistry,Nankai University,Tianjin). Studies on the Aromatic Dihalocarbonyl Ylides and Their Deoxygenation[J]. 高等学校化学研究, 1989, 0(1)
作者姓名:Huan Zhenwei  Pan Yinming  Qu Xiaosu and Gao Zhenheng (Department of Chemistry  Nankai University  Tianjin)
作者单位:Department of Chemistry,Nankai University,Tianjin
摘    要:The deoxygenation reaction of heptanones, cycloheptanone, cycloheptatrienone or substituted cycloheptatrienone with dihalo-carbene results in carbon monoxide and corresponding halides. The yield of CO produced by 2 , 4 , 6-triphenylcycloheptatrienone is 2.6-3.5 times as high as that produced by the saturated heptanones. The structures, energies, charge distributions, bond orders, and other relative parameters of the dihalocarbonyl glides were calculated by using the SCF-MNDO method. The obtained data reveal that the ylides from cycloheptatrienone have aromatic structure and are different from those produced from saturated cycloheptanone. The reactivities of the dihalocarbonyl ylides are discussed. It is proposed that this aromatic structure should be responsible for the high yield of CO from the reaction of cycloheptatrienone with dihalocarbene.


Studies on the Aromatic Dihalocarbonyl Ylides and Their Deoxygenation
Huan Zhenwei,Pan Yinming,Qu Xiaosu and Gao Zhenheng. Studies on the Aromatic Dihalocarbonyl Ylides and Their Deoxygenation[J]. Chemical Research in Chinese University, 1989, 0(1)
Authors:Huan Zhenwei  Pan Yinming  Qu Xiaosu  Gao Zhenheng
Abstract:The deoxygenation reaction of heptanones, cycloheptanone, cycloheptatrienone or substituted cycloheptatrienone with dihalo-carbene results in carbon monoxide and corresponding halides. The yield of CO produced by 2 , 4 , 6-triphenylcycloheptatrienone is 2.6-3.5 times as high as that produced by the saturated heptanones. The structures, energies, charge distributions, bond orders, and other relative parameters of the dihalocarbonyl glides were calculated by using the SCF-MNDO method. The obtained data reveal that the ylides from cycloheptatrienone have aromatic structure and are different from those produced from saturated cycloheptanone. The reactivities of the dihalocarbonyl ylides are discussed. It is proposed that this aromatic structure should be responsible for the high yield of CO from the reaction of cycloheptatrienone with dihalocarbene.
Keywords:Carbonyl ylide   Deoxygenation   Aromaticity.
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