A New Reaction for the Generation of Carbene from α-Amino Acid and Ketone

Chin. J. Org. Chem. ›› 2007, Vol. 27 ›› Issue (12): 1609-1611. Previous Articles Next Articles

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一个由α-氨基酸和酮产生卡宾的新反应

郑大贵*^,a，肖竹平^a，李玉良^b

(^a上饶师范学院化学系上饶 334001)
(^b中国科学院化学研究所北京 100080)

收稿日期:2007-08-12 修回日期:2007-09-29 发布日期:2007-12-04

通讯作者: 郑大贵

A New Reaction for the Generation of Carbene from α-Amino Acid and Ketone

ZHENG Da-Gui*^,a, XIAO Zhu-Ping^a, LI Yu-Liang^b

(^aDepartment of Chemistry, Shangrao Normal College, Shangrao 334001)
(^bInstitute of Chemistry, Chinese Academy of Sciences, Beijing 100080)

Received:2007-08-12 Revised:2007-09-29 Published:2007-12-04

Contact: ZHENG Da-Gui

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Abstract

2-Phenyl-1-chloro-1-trichloroacetylcyclopropane (3) was obtained from the reaction of styrene with carbene generated by refluxing the mixture of DL-valine and hexachloroacetone in chlorobenzene under an atmosphere of nitrogen_. The structure of 3 was characterized by FT-IR, EI-MS and ¹H NMR spectra. The possible reaction mechanism was suggested.

Key words: hexachloroacetone, carbene, azomethine ylide, DL-valine

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ZHENG Da-Gui*^,a, XIAO Zhu-Ping^a, LI Yu-Liang^b. A New Reaction for the Generation of Carbene from α-Amino Acid and Ketone[J]. Chin. J. Org. Chem., 2007, 27(12): 1609-1611.

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[1]	Dengpeng Xia, Jinyun Luo, Lin He, Zhihua Cai, Guangfen Du. N-Heterocyclic Carbene-Catalyzed Synthesis of Pentafluorophenyl Sulfides [J]. Chinese Journal of Organic Chemistry, 2024, 44(2): 622-630.
[2]	Shuang Yang, Xinqiang Fang. Kinetic Resolutions Enabled by N-Heterocyclic Carbene Catalysis: An Update [J]. Chinese Journal of Organic Chemistry, 2024, 44(2): 448-480.
[3]	Yuanlin Cai, Ya Lü, Guihua Nie, Zhichao Jin, Yonggui Chi. Recent Advances in the Synthesis of Cyanides Enabled by N-Heterocyclic Carbene Catalysis [J]. Chinese Journal of Organic Chemistry, 2023, 43(9): 3135-3145.
[4]	Zuliang Chen, Yingjing Wei, Junliang Zhang. Recent Advances in Cycloaddition Reactions of Donor-Acceptor Aziridines via Carbon-Carbon Bond Cleavage [J]. Chinese Journal of Organic Chemistry, 2023, 43(9): 3078-3088.
[5]	Xiaoping Xu, Yifei Zhang, Xiaoyu Mo, Jun Jiang. Rh-Catalyzed C—H Functionalization Reaction between 3-Diazoindolin-2-imines and Pyrazolones for the Construction of 3-Pyrazolyl Indoles [J]. Chinese Journal of Organic Chemistry, 2023, 43(7): 2519-2527.
[6]	Liangru Yang, Mengli Guo, Jinwei Yuan, Jiamei Wangx, Yuting Xia, Yongmei Xiao, Pu Mao. Research Progress on Pincer N-Heterocyclic Carbene Metal Complexes [J]. Chinese Journal of Organic Chemistry, 2023, 43(6): 2002-2025.
[7]	Zhihao Chen, Qi Fan, Biaolin Yin, Qingjiang Li, Honggen Wang. Progress in the Syntheses of α-Boryl Carbonyl Compounds [J]. Chinese Journal of Organic Chemistry, 2023, 43(5): 1706-1712.
[8]	Xinyu Zhang, Huihui Geng, Shilei Zhang, Wei Wang, Xiaobei Chen. A Method for the Synthesis of Deuterated Benzoins Catalyzed by N-Heterocyclic Carbene [J]. Chinese Journal of Organic Chemistry, 2023, 43(4): 1510-1516.
[9]	Hua Huang, Xin Li, Jianke Su, Qiuling Song. Difluorocarbene-Enabled Synthesis of 3-Substituted-2-oxoindoles from o-Vinylanilines [J]. Chinese Journal of Organic Chemistry, 2023, 43(3): 1146-1156.
[10]	Chunbo Dai, Siqi Xia, Xiaoyu Chen, Limin Yang. N-Heterocyclic Carbene (NHC)-Catalyzed [4+3] Cycloaddition to Synthesize 4-Aminobenzoheptenolactons [J]. Chinese Journal of Organic Chemistry, 2023, 43(3): 1084-1090.
[11]	Tingting Liu, Yucai Hu, An Shen. Mechanism of Carbon-Carbon Coupling Reactions Catalyzed by Imine-Ligand-Assisted N-Heterocyclic Carbene Palladium Complexes [J]. Chinese Journal of Organic Chemistry, 2023, 43(2): 622-628.
[12]	Guijie Liu, Zhengqiang Fu, Fei Chen, Caixia Xu, Min Li, Ning Liu. N-Heterocyclic Carbene-Pyridine Manganese Complex/ Tetrabutylammonium Iodide Catalyzed Synthesis of Cyclic Carbonate from CO₂ and Epoxide [J]. Chinese Journal of Organic Chemistry, 2023, 43(2): 629-635.
[13]	Zhi Tu, Jinsheng Yu, Jian Zhou. Synthesis of (Bromodifluoromethyl)trimethylsilane and Its Applications in Organic Synthesis [J]. Chinese Journal of Organic Chemistry, 2023, 43(10): 3491-3507.
[14]	Dan Ba, Guolin Cheng. Blue Light Induced Insertion of Carbene into C(CO)—C Bonds of 1,3-Diones [J]. Chinese Journal of Organic Chemistry, 2022, 42(9): 2888-2897.
[15]	Wei Zhao, Jing Liu, Xiangkui He, Hao Jiang, Liangqiu Lu, Wenjing Xiao. N-Heterocyclic Carbene (NHC)-Catalyzed Desymmetrization of Biaryldialdehydes to Construct Axially Chiral Aldehydes [J]. Chinese Journal of Organic Chemistry, 2022, 42(8): 2504-2514.