Studies on the regioslectivity of addition reaction of girgnard reagents to α-cinnamoyl ketene dithioacetals-the modulation by alkylthio groups

Chin. J. Org. Chem. ›› 2001, Vol. 21 ›› Issue (9): 676-680. Previous Articles Next Articles

α-肉桂酰基二硫缩烯酮与Grignard试剂的加成反应区域选择研究-烷硫基对反应的调控作用

林春;赵彩虹;刘群;胡玉兰;方群欣;齐巍

靶山师范学院化学系;东北师范大学化学系.长春(130024)

发布日期:2001-09-25

Studies on the regioslectivity of addition reaction of girgnard reagents to α-cinnamoyl ketene dithioacetals-the modulation by alkylthio groups

Lin Chun;Zhao Caihong;Liu Qun;Hu Yulan;Fang Qunxin;Qi Wei

NE Normal Univ, Dept Chem.Changchun(130024)

Published:2001-09-25

Abstract

The addition reaction of entyl, n-butyl, phenyl and benzyl Grignard reagents to α-cinnamoyl ketene dithioacetals which with 1, 3- propylenedithio or 1, 4-butylenedithio and diethylthio groups was studied. The conjuagted additional products at the carbon atom adjacent to aryl were obtained. When the alkylthio group was dimenethylthio, the products were so complicated that attempted seperation(silica gel) was failed. A probe reaction showed that the diethylthio group had different adjustment to this modulation reaction comparing with dimethylthio group in α-oxo ketene dithioacetls.

Key words: CARBONYL GROUP, DITHIO-, KENONE P, ADDITION REACTION, ALKYLTHIO GROUP, CINNAMIC ACID P, GRIGNARD REAGENT

CLC Number:

O621

Cite this article

Lin Chun;Zhao Caihong;Liu Qun;Hu Yulan;Fang Qunxin;Qi Wei. Studies on the regioslectivity of addition reaction of girgnard reagents to α-cinnamoyl ketene dithioacetals-the modulation by alkylthio groups[J]. Chin. J. Org. Chem., 2001, 21(9): 676-680.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

[1]	Zujia Chen, Shiwei Yu, Yongjun Zhou, Huanqing Li, Qiwen Qiu, Miaoxin Li, Zhaoyang Wang. Application of BF₃•OEt₂ in Organic Synthesis as a Catalyst or Synthon [J]. Chinese Journal of Organic Chemistry, 2023, 43(9): 3107-3118.
[2]	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.
[3]	Min Lü, Aimei Yang, Yu Zhang, Jianting Sun, Bangguo Wei. Fe(OTf)₃-Catalyzed Synthesis of Boronic Ester Containing N,O-Acetal Structure [J]. Chinese Journal of Organic Chemistry, 2023, 43(5): 1777-1785.
[4]	Deliang Kong, Wen Dai, Yiling Zhao, Yilin Chen, Hongping Zhu. Study on Oxidative Cycloaddition Reactions of Amidinatoboryl-aminosilylenes toward Ketone and Diketone Molecules [J]. Chinese Journal of Organic Chemistry, 2023, 43(5): 1843-1851.
[5]	Luomo Li, Xiaohui Yang. Recent Advances in Ionic Transfer Reactions [J]. Chinese Journal of Organic Chemistry, 2023, 43(3): 1036-1044.
[6]	Junxiu Liang, Yazhou Liu, Amu Wang, Yanchao Wu, Xiaofeng Ma, Huijing Li. Dearomatization of Halonaphthols via an Intermolecular [4＋1] Spiroannulation with in situ Formed Aza-ortho-quinone Methides [J]. Chinese Journal of Organic Chemistry, 2023, 43(11): 3888-3899.
[7]	Junjiao Wang, Yuyu Lv, Yongwei Shang, Zhenli Cui, Ke-Hu Wang, Danfeng Huang, Yulai Hu. Research Progress of Reactions Participated by α-Hydroxy Ketones [J]. Chinese Journal of Organic Chemistry, 2022, 42(8): 2300-2321.
[8]	Haoru Song, Jianting Sun, Min LÜ, Yiwen Liu, Bangguo Wei. Trifluoromethyl Sulfonic Anhydride Mediated Addition of Pyridine with Ynamides [J]. Chinese Journal of Organic Chemistry, 2022, 42(8): 2433-2437.
[9]	Donglan Liu, Haiyan Xu, Yi Hang, Hongfei Lu. 1,6-Addition of Nitrogen Nucleophile to para-Quinone Methides Catalyzed by Recyclable Bismuth Complex: Facile Access to N-Heterocyclic Substituted Unsymmetric Triarylmethane Derivatives [J]. Chinese Journal of Organic Chemistry, 2022, 42(3): 796-802.
[10]	Honghua Zuo, Fangrui Zhong. Reactivity Modulation of Labile Quinones and Biomimetic Catalytic Transformations [J]. Chinese Journal of Organic Chemistry, 2022, 42(3): 665-678.
[11]	Yuyu Guo, Xiangjie Chen, Shiwu Li, Zhihua Cai, Lin He. Synthesis of Mutisubstituted Dihydropyridino[1,2-a]benzimidazole Derivatives via Tandem Reaction of 2-Arylbenzimidazoles [J]. Chinese Journal of Organic Chemistry, 2021, 41(9): 3692-3700.
[12]	Jiabing Sun, Tao Miao, Pinhua Li, Lei Wang. t-BuOK-Mediated Reductive Desulfonylation/Dehydrogenation for the Synthesis of 2-Substituted 1,3-Dienes and Their [4+2] Cycloaddition Reactions [J]. Chinese Journal of Organic Chemistry, 2021, 41(8): 3144-3156.
[13]	Zhenli Xu, Zongxue Zhang, Chenxiang Meng, Xiaoya Zhang, Kai Xu, Lantao Liu, Tao Wang, Haiyun Xu, Guoliang Mao. Ligand-Free Pd-Catalyzed Hydrophosphorylation of Internal Alkynes for the Synthesis of E-Vinylphosphonates [J]. Chinese Journal of Organic Chemistry, 2021, 41(8): 3264-3271.
[14]	Qiang Yan, Rong Fan, Binbin Liu, Shuaisong Su, Bo Wang, Tuanli Yao, Jiajing Tan. Recent Progress in Aryne Participated Dearomatization Reactions [J]. Chinese Journal of Organic Chemistry, 2021, 41(2): 455-470.
[15]	Ning Zou, Xiaoting Qin, Zhixin Wang, Weimin Shi, Dongliang Mo. Advances on the Synthesis and Application of α,β-Unsaturated Nitrones [J]. Chinese Journal of Organic Chemistry, 2021, 41(12): 4535-4553.

α-肉桂酰基二硫缩烯酮与Grignard试剂的加成反应区域选择研究-烷硫基对反应的调控作用

Studies on the regioslectivity of addition reaction of girgnard reagents to α-cinnamoyl ketene dithioacetals-the modulation by alkylthio groups

PDF

Knowledge

Abstract

Cite this article

share this article

References

Related Articles 15

Recommended Articles

Metrics

Comments

α-肉桂酰基二硫缩烯酮与Grignard试剂的加成反应区域 选择研究-烷硫基对反 应的调控作用

Studies on the regioslectivity of addition reaction of girgnard reagents to α-cinnamoyl ketene dithioacetals-the modulation by alkylthio groups

PDF

Knowledge

Abstract

Cite this article

share this article

References

Related Articles 15

Recommended Articles

Metrics

Comments

α-肉桂酰基二硫缩烯酮与Grignard试剂的加成反应区域选择研究-烷硫基对反应的调控作用