Convenient Synthesis of Olefins from Tertiary Alcohols under Mild Basic Condition

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Chin. J. Org. Chem. ›› 2005, Vol. 25 ›› Issue (06): 727-729. Previous Articles Next Articles

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弱碱作用下从叔醇简便地合成烯烃

李新生*^,1，葛健锋²，胡晓春¹

(¹浙江师范大学化学系金华 321004)
(²苏州大学材料工程学院苏州 215006)

收稿日期:2004-06-21 修回日期:2004-12-14 发布日期:2005-05-30
通讯作者: 李新生

Convenient Synthesis of Olefins from Tertiary Alcohols under Mild Basic Condition

LI Xin-Sheng*¹, GE Jian-Feng², HU Xiao-Chun¹

(¹ Department of Chemistry and Biology, Zhejiang Normal University, Jinhua 321004)
(² Department of Material and Engineering, Suzhou University, Suzhou 215006)

Received:2004-06-21 Revised:2004-12-14 Published:2005-05-30

Contact: LI Xin-Sheng

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Abstract

An efficient method has been achieved for the dehydration of tertiary alcohols using the combination of methanesulfonic anhydride and triethylamine as dehydration agent to obtain olefin in high yield. The short reaction time, mild basic conditions and high yield make it a facile way for the synthesis of olefins from tertiary alcohols.

Key words: olefin, dehydration, tertiary alcohol

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LI Xin-Sheng*¹, GE Jian-Feng², HU Xiao-Chun. Convenient Synthesis of Olefins from Tertiary Alcohols under Mild Basic Condition[J]. Chin. J. Org. Chem., 2005, 25(06): 727-729.

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[1] Jie Liu, Feng Han, Shuangyan Li, Tianyu Chen, Jianhui Chen, Qing Xu. Transition Metal-Free Selective Aerobic Olefination of Methyl N-Heteroarenes with Alcohols [J]. Chinese Journal of Organic Chemistry, 2024, 44(2): 573-583.

[2] Hong'en Tong, Hongyu Guo, Rong Zhou. Progress on Visible-Light Promoted Addition Reactions of Inert C—H Bonds to Carbonyls [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 54-69.

[3] Hongyu Hou, Yuanyuan Cheng, Bin Chen, Chenho Tung, Lizhu Wu. α-Acylation of Olefins via Photocatalysis [J]. Chinese Journal of Organic Chemistry, 2023, 43(3): 1012-1022.

[4] Ping Guo, Yong Zhou, Jie Zhao. Z∶E Selective Preparation of Disubstituted Internal Alkenes and Trisubstituted Alkenes [J]. Chinese Journal of Organic Chemistry, 2023, 43(3): 855-872.

[5] Luomo Li, Xiaohui Yang. Recent Advances in Ionic Transfer Reactions [J]. Chinese Journal of Organic Chemistry, 2023, 43(3): 1036-1044.

[6] Biao Han, Yaoyao Zhang, Shuhan Chen, Mengge Zhao, Nan Li, Weishuang Li, Lei Zhu. Preparation of Axially Grafted Temperature-Responsive Chiral Salen Mn^III and Application in Asymmetric Epoxidation of Olefins in Water [J]. Chinese Journal of Organic Chemistry, 2023, 43(1): 244-253.

[7] Zhaohua Chen, Xiying Cao, Sihong Chen, Shiwei Yu, Yanlan Lin, Shuting Lin, Zhaoyang Wang. Design, Synthesis and Application of Trisubstituted Olefinic Aggregation-Induced Emission Molecules [J]. Chinese Journal of Organic Chemistry, 2022, 42(8): 2355-2363.

[8] Haiqiong Li, Mengyun Yin, Fenfen Xie, Zhengbing Zhang, Pan Han, Linhai Jing. Synthesis of Nitrile via Electrochemical Appel Reaction [J]. Chinese Journal of Organic Chemistry, 2022, 42(7): 2229-2235.

[9] Yunrong Chen, Wei Liu, Xiaoyu Yang. Recent Advances in Kinetic Resolution of Tertiary Alcohols [J]. Chinese Journal of Organic Chemistry, 2022, 42(3): 679-697.

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[12] Yingjie Liu, Yinghui Han, Liqing Lin, Ying Xu. Research Progress of Polyfluoroalkylation Reaction under Electrochemical Catalysis [J]. Chinese Journal of Organic Chemistry, 2021, 41(3): 934-946.

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[15] Bing Mu, Junliang Wu, Guang'an Zhang. Alternative Approach for the Synthesis of Nitroaromatic Olefins via Dehydrogenative Nitration of Easily Available Arylethanes [J]. Chinese Journal of Organic Chemistry, 2021, 41(1): 250-257.

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[1]	Jie Liu, Feng Han, Shuangyan Li, Tianyu Chen, Jianhui Chen, Qing Xu. Transition Metal-Free Selective Aerobic Olefination of Methyl N-Heteroarenes with Alcohols [J]. Chinese Journal of Organic Chemistry, 2024, 44(2): 573-583.
[2]	Hong'en Tong, Hongyu Guo, Rong Zhou. Progress on Visible-Light Promoted Addition Reactions of Inert C—H Bonds to Carbonyls [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 54-69.
[3]	Hongyu Hou, Yuanyuan Cheng, Bin Chen, Chenho Tung, Lizhu Wu. α-Acylation of Olefins via Photocatalysis [J]. Chinese Journal of Organic Chemistry, 2023, 43(3): 1012-1022.
[4]	Ping Guo, Yong Zhou, Jie Zhao. Z∶E Selective Preparation of Disubstituted Internal Alkenes and Trisubstituted Alkenes [J]. Chinese Journal of Organic Chemistry, 2023, 43(3): 855-872.
[5]	Luomo Li, Xiaohui Yang. Recent Advances in Ionic Transfer Reactions [J]. Chinese Journal of Organic Chemistry, 2023, 43(3): 1036-1044.
[6]	Biao Han, Yaoyao Zhang, Shuhan Chen, Mengge Zhao, Nan Li, Weishuang Li, Lei Zhu. Preparation of Axially Grafted Temperature-Responsive Chiral Salen Mn^III and Application in Asymmetric Epoxidation of Olefins in Water [J]. Chinese Journal of Organic Chemistry, 2023, 43(1): 244-253.
[7]	Zhaohua Chen, Xiying Cao, Sihong Chen, Shiwei Yu, Yanlan Lin, Shuting Lin, Zhaoyang Wang. Design, Synthesis and Application of Trisubstituted Olefinic Aggregation-Induced Emission Molecules [J]. Chinese Journal of Organic Chemistry, 2022, 42(8): 2355-2363.
[8]	Haiqiong Li, Mengyun Yin, Fenfen Xie, Zhengbing Zhang, Pan Han, Linhai Jing. Synthesis of Nitrile via Electrochemical Appel Reaction [J]. Chinese Journal of Organic Chemistry, 2022, 42(7): 2229-2235.
[9]	Yunrong Chen, Wei Liu, Xiaoyu Yang. Recent Advances in Kinetic Resolution of Tertiary Alcohols [J]. Chinese Journal of Organic Chemistry, 2022, 42(3): 679-697.
[10]	San'e Zhu, Lifeng Dou, Jianhui Zhang, Ying Wu, Wei Yang, Hongdian Lu, Chunxiang Wei, Chonghai Deng, Qiang Dong. Palladium-Catalyzed Synthesis of Dihydrofuran-Fused [60]Fullerene Derivatives via Heteroannulation of Olefins [J]. Chinese Journal of Organic Chemistry, 2021, 41(5): 2082-2090.
[11]	Yongqing Li, Fan Wang, Yucai Cao. Late Transition Metal Complexes for Olefin Copolymerization with Polar Monomers [J]. Chinese Journal of Organic Chemistry, 2021, 41(4): 1396-1433.
[12]	Yingjie Liu, Yinghui Han, Liqing Lin, Ying Xu. Research Progress of Polyfluoroalkylation Reaction under Electrochemical Catalysis [J]. Chinese Journal of Organic Chemistry, 2021, 41(3): 934-946.
[13]	Hengding Wang, Ling Jiang, Hongyan Liang, Hongjun Fan. Mechanism of Silver-Catalyzed [2+2] Cycloaddition between Siloxy-Alkynes and Carbonyl Compound: A Silylium Ion Migration Approach [J]. Chinese Journal of Organic Chemistry, 2021, 41(11): 4327-4337.
[14]	Huaiyuan Zhang, Thomas Wirth. Recent Advances in Asymmetric Functionalization of Olefins Induced by Chiral Hypervalent Iodine Reagents [J]. Chinese Journal of Organic Chemistry, 2021, 41(1): 65-70.
[15]	Bing Mu, Junliang Wu, Guang'an Zhang. Alternative Approach for the Synthesis of Nitroaromatic Olefins via Dehydrogenative Nitration of Easily Available Arylethanes [J]. Chinese Journal of Organic Chemistry, 2021, 41(1): 250-257.