The reaction of the ω-(methylsulfinyl)acetophenone with p-nitrobenzyl derivatives

Abstract

The anion of w-(methylsulfinyl)acetophenone reacts with 4-O2NC6H4CH2R (R = Cl, Br, iodo, Me3N+ I-) at room temperature via C-alkylation and elimination to give w-(4-nitrobenzylidene)acetophenone. The C-alkylation of the p-nitrobenzyl derivatives with poor leaving groups by anion has been demonstrated to proceed via the SRN1 mechanism.

Key words: NITRO COMPOUNDS, REACTION MECHANISM, SUBSTITUTION REACTION, REARRANGEMENT REACTION, ELECTRON TRANSFER, BENZYL GROUP, ACETOPHENONE P, ANION, NUCLEOPHILIC REACTION, AROMATIC COMPOUNDS, SULFOXIDE P

CLC Number:

O621

Cite this article

HONG LIN;CHEN LIYA;YANG KE;ZHAO YONGGEN. The reaction of the ω-(methylsulfinyl)acetophenone with p-nitrobenzyl derivatives[J]. Chin. J. Org. Chem., 1988, 8(2): 128-130.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

[1]	Lijun Xu, Zongjun Li, Fushe Han, Xiang Gao. N,N-Dimethylformamide-Promoted Synthesis of Fullerene-Fused Oxazoline Derivatives [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 242-250.
[2]	Huanqing Li, Zhaohua Chen, Zujia Chen, Qiwen Qiu, Youcai Zhang, Sihong Chen, Zhaoyang Wang. Research Progress in Mercury Ion Fluorescence Probes Based on Organic Small Molecules [J]. Chinese Journal of Organic Chemistry, 2023, 43(9): 3067-3077.
[3]	Wei Xu, Hongbin Zhai, Bin Cheng, Taimin Wang. Visible Light-Induced Pd-Catalyzed Heck Reactions [J]. Chinese Journal of Organic Chemistry, 2023, 43(9): 3035-3054.
[4]	Xiaona Yang, Hongyu Guo, Rong Zhou. Progress in Visible-Light Promoted Transformations of Organosilicon Compounds [J]. Chinese Journal of Organic Chemistry, 2023, 43(8): 2720-2742.
[5]	Wenhan Yang, Jiwen Jiao, Xiaoming Wang. Merging Electron Transfer Activation with 1,2-Metalate Migration: Deoxygenative Silylation of Amides [J]. Chinese Journal of Organic Chemistry, 2023, 43(5): 1857-1867.
[6]	Cunjing Miao, Jiaqi Yao. Recent Advances in the Transformation Reactions of Aromatic Nitriles via C—CN Bond Cleavage [J]. Chinese Journal of Organic Chemistry, 2023, 43(4): 1341-1364.
[7]	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.
[8]	Yueling Liu, Xinxin Zhong, Ganbing Zhang. Density Functional Theory Study for Exploring the Mechanisms of the [3＋2] Cycloaddition Reactions between 1-R-3-Phenylpropylidenecyclopropane (R=Me/H) and Furfural Catalyzed by Pd(0) [J]. Chinese Journal of Organic Chemistry, 2023, 43(2): 660-667.
[9]	Yuheng Wu, Yan Yan, Weiwei Liao. Recent Advances of Bifunctional Sulfur Dioxide Surrogates in Synthesis of Sulfonyl Compounds [J]. Chinese Journal of Organic Chemistry, 2023, 43(11): 3713-3727.
[10]	Zhaoming Hu, Jihong Wu, Jingjing Wu, Fanhong Wu. Research Progress on Direct Trifluoromethylselenylation [J]. Chinese Journal of Organic Chemistry, 2023, 43(1): 36-56.
[11]	Geyang Song, Dong Xue. Research Progress on Light-Promoted Transition Metal-Catalyzed C-Heteroatom Bond Coupling Reactions [J]. Chinese Journal of Organic Chemistry, 2022, 42(8): 2275-2299.
[12]	Yan Huang, Qian Zhang, Lewu Zhan, Jing Hou, Bindong Li. Hydrocarboxylation of Alkenes with Formate Salts via Photocatalysis [J]. Chinese Journal of Organic Chemistry, 2022, 42(8): 2568-2573.
[13]	Zexin Huang, Yuqiang Yin, Fengcheng Jia, Anxin Wu. Research Progress on C2—C3 Bond Cleavage of Indole and Its Derivatives [J]. Chinese Journal of Organic Chemistry, 2022, 42(7): 2028-2044.
[14]	Liwen Ma, Xiaoye Wei, Zilin Zhao, Ang Zhao, Xiangwen Deng, Bingnan Huo, Gang Ma, Chunfang Zhang. Theoretical Study on the Catalytic Mechanism of Copper with Various Valence for the Terminal Alkyne Coupling Reaction [J]. Chinese Journal of Organic Chemistry, 2022, 42(6): 1811-1819.
[15]	Yubing Shi, Wenji Bai, Weihua Mu, Jiangping Li, Jiawei Yu, Bing Lian. Research Progress on Density Functional Theory Study of Palladium-Catalyzed C—H Functionalization to Form C—X (X=O, N, F, I, …) Bonds [J]. Chinese Journal of Organic Chemistry, 2022, 42(5): 1346-1374.

ω-甲亚砜基苯乙酮阴离子与对硝基苄基衍生物的反应