Studies on the hydrosilation of allyl acetate

Abstract

The dependence of reactivity on mol. structure in the hydrosilation of allyl acetate catalyzed by (Ph3P)3RhCl was studied by kinetics. The results showed that: a) the reaction constant of model reaction I, in which AcOCH2CH:CH2 was hydrosilylated with I (R = Ph, p-tolyl, p-anisyl, p-ClC6H4, p-FC6H4), is 3.26 and the rate is increased by electron-withdrawing groups, b) the rate of model reaction II, in which AcOCH2CH:CH2 was hydrosilylated with I (R = Me, Et, Me2CH, Me3C), is decreased when the size of R becomes larger.

Key words: REACTION KINETICS, GAS CHROMATOGRAPHY, ALLYL ACETATE, PROTON MAGNETIC RESONANCE SPECTROMETRY, RHODIUM COMPLEX, TRIPHENYLPHOSPHINE

CLC Number:

O621

Cite this article

CHEN LI;XU SHANSHENG;LI XIN;ZHOU XIUZHONG. Studies on the hydrosilation of allyl acetate[J]. Chin. J. Org. Chem., 1992, 12(1): 91-95.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

[1]	Chen Liang, Hu Liangjian, Du Yu, Su Weiping, Kang Qiang. Asymmetric Photoinduced Giese Radical Addition Enabled by a Single Chiral-at-Metal Rhodium Complex [J]. Chinese Journal of Organic Chemistry, 2020, 40(11): 3944-3952.
[2]	Xiao Yuanyuan, Wang Youming, Zhou Zhenghong. Asymmetric Synthesis of Novel Fused Polycyclic 3,4-Dihydro-pyrano[4,3-b]pyran-5(2H)-ones via an Organocatalyzed Formal[3+3] Annulation [J]. Chin. J. Org. Chem., 2019, 39(8): 2203-2210.
[3]	Zhao Xia, Li Tianjiao, Tian Miaomiao, Su Zhiyang, Wei Aoqi, Lu Kui. Triphenylphosphine Mediated Direct Trifluoromethylthiolation of Indolizine and Pyrrole by Trifluoromethanesulfonyl Chloride [J]. Chin. J. Org. Chem., 2018, 38(3): 677-683.
[4]	ZHANG Xue-Sheng, SHI Jia-Qi, SUN Li, WANG Zun-Yao. Palladium-Catalyzed Carbon-Sulfur Bond Formation to Synthesize Polychlorinated Diphenyl Sulfides [J]. Chin. J. Org. Chem., 2011, 31(07): 1107-1113.
[5]	SUN Huai-Lin*,HUANG Xue-Bin,TENG Xiang-Dang. Synthesis and Molecular Structure of Si—Fe Bond-Containing Cyclic Complexes [Me₂Si-η⁵-C₅H₄Fe(CO)(PPh₃)][Me₂Si-η⁵- C₅H₄Fe(CO)_{[J]. Chin. J. Org. Chem., 2006, 26(03): 324-328.}
[6]	CHENG, Sen-Xiang, WANG, Li-Min, CHANG, Jun-Biao, QU, Ling-Bo, CHEN, Xiao-Lan, CHEN, Rong-Feng. Synthesis of 4,4′-Dimethoxy-5,6,5′,6′-dimethenedioxy-2-alkyloxycarbonyl-2′-(4-substituted benzyl piperazin-1-yl)carbonyl-biphenyl [J]. Chinese Journal of Organic Chemistry, 2004, 24(6): 691-696.
[7]	DONG, Xiao-Wei, XU, Xu, JIN, Hao, LI, Zu-Yi. Separation of Chloro-substituted and Bromo-substituted Styrene Oxide by Chiral GC [J]. Chinese Journal of Organic Chemistry, 2004, 24(3): 306-309.
[8]	Su Weike;Liang Xianrui;Li Yongshu;Zhang Yongmin. A Convenient One-Pot Procedure for the Preparation of Disulfides from Thiols [J]. Chin. J. Org. Chem., 2003, 23(9): 1019-1021.
[9]	Xiong Junru;Xiang Qingxiang;Zhang Yuanqin. Synthesis and Liquid Crystal Behavior of 3-Alkoxy-6-(4- methoxycarbonylphenyl) pyridazines [J]. Chin. J. Org. Chem., 2003, 23(8): 832-835.
[10]	Zhang Zhanjin;Wan Boshun;Chen Huilin. Progress of Application of Chiral Binuclear Complex Catalyst to the Asymmetric Synthesis [J]. Chin. J. Org. Chem., 2003, 23(7): 636-645.
[11]	Yang Fengling;Wang Hongqing;Cao Hong;Liu Zhaojie. Studies on the Rearrangement Reaction of Propargyl Thionophosphates in GC Capillary Column [J]. Chin. J. Org. Chem., 2003, 23(5): 461-465.
[12]	Tang Xinde;ZHang Qizhen;Zhou Qifeng. Star-Shaped Liquid Crystals:Synthesis,Phase Behavior and Applications [J]. Chin. J. Org. Chem., 2003, 23(1): 100-103.
[13]	Qing Zhenglong. Molecular topological research on physical and chemical properties of aliphatic alcohols [J]. Chin. J. Org. Chem., 2002, 22(6): 436-439.
[14]	She Zhigang;Hu Guping;Wu Yaowen;Lin Yongcheng. Study on the methanolysis of the sulphated polysaccharide hal-a from haliotis diverisicolor reeve [J]. Chin. J. Org. Chem., 2002, 22(5): 367-370.
[15]	Zhang Jingchang;Cao Weiliang;Lin Yanjun;Wei Hongliang. Synthesis of tetraphenylphosphonium bromide [J]. Chin. J. Org. Chem., 2001, 21(8): 614-617.

乙酸烯丙酯的氢硅化反应