Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, China, Halogenation through Deoxygenation of Alcohols and Aldehydes. Lett., Yadong Gao, Chao Yang, Jing Wang, Chao Jiang, Xiangbing Qi. Abstract. Ranganayakulu Sunnapu, Saikumar Naik Banoth, Reyno R. S., Aleena Thomas, Navyasree Venugopal. The use of (EtO) 3 P instead of Ph 3 P enables a convenient purification process, as the byproduct (EtO) 3 P═O could be removed by aqueous washing. If you do not receive an email within 10 minutes, your email address may not be registered, system. We use cookies to help provide and enhance our service and tailor content and ads. alkyl iodides. Copper-Catalyzed Dichloromethylazidation of Alkenes Using BrCCl2H as a Stoichiometric Dichloromethylating Reagent. The amount of thiourea added dictates the pathway of the reaction, which may diverge from the desired halogenation reaction toward oxidation of the alcohol, in the absence of thiourea, or toward starting material recovery when excess thiourea is used. Information. redistribute this material, requesters must process their own requests via the RightsLink permission Article Views are the COUNTER-compliant sum of full text article downloads since November 2008 (both PDF and HTML) across all institutions and individuals. By continuing you agree to the use of cookies. the Altmetric Attention Score and how the score is calculated. Users are The resulting product is a vicinal (neighboring) dihalide. An efficient reagent system, Ph3P/XCH2CH2X (X = Cl, Br, or I), was very effective for the deoxygenative halogenation (including fluorination) of alcohols (including tertiary alcohols) and aldehydes. Xuan Xiao, Xu Yao, Jiao Yu, Ting Tang, Can Xiao, Jinying Gu, Jin-Hong Lin, Xing Zheng, Ji-Chang Xiao. Shareable Link. benzyl chlorides, These metrics are regularly updated to reflect usage leading up to the last few days. Please note: If you switch to a different device, you may be asked to login again with only your ACS ID. Ask Question Asked 7 years, 2 months ago. Organocatalytic Chlorination of Alcohols by P(III)/P(V) Redox Cycling. Synthesis of chromeno[4,3- Information about how to use the RightsLink permission system can be found at This article has not yet been cited by other publications. Browse other articles of this reference work: The full text of this article hosted at iucr.org is unavailable due to technical difficulties. Peigen Su, Chao Fan, Heng Yu, Wanqin Wang, Xin Jia, Qifan Rao, Chenxi Fu, Donghua Zhang, Benhua Huang, Cheng Pan, Aqun Zheng, Yang Sun. Use the link below to share a full-text version of this article with your friends and colleagues. The present invention relates to the halogenation of tertiary alcohols and more particularly to the chlorination and bromination of tertiary butyl and tertiary amyl alcohols. https://doi.org/10.1016/j.tetlet.2016.04.083. The easily available 1,2-dihaloethanes were used as key reagents and halogen sources. 21 publications. Ya-Xuan Zhang, Ruo-Xing Jin, Han Yin, Yan Li. Copyright © 2020 Elsevier B.V. or its licensors or contributors. Your Mendeley pairing has expired. View the article PDF and any associated supplements and figures for a period of 48 hours. Active 3 years, 7 months ago. 1,1-dibromides, Find more information on the Altmetric Attention Score and how the score is calculated. Learn about our remote access options, Chemistry Department, Iowa State University, Ames, IA, USA, Chemical Development, Boehringer Ingelheim Pharmaceuticals, Inc., Ridgefield, CT, USA. Citations are the number of other articles citing this article, calculated by Crossref and updated daily. The use of (EtO) 3 P instead of Ph 3 P enables a convenient purification process, as the byproduct (EtO) 3 P═O could be removed by aqueous washing. The alkyl halides have been utilized in the synthesis of many effective drugs. Viewed 3k times 3. Learn more. Find more information about Crossref citation counts. Active 3 years, 7 months ago. not otherwise permitted to reproduce, republish, redistribute, or sell any Supporting Information A dehydroxy-fluorination proceeds well in without permission from the American Chemical Society. Detailed electron paramagnetic resonance (EPR) studies, isotopic labeling, and other control experiments suggest a radical-based mechanism. without permission from the American Chemical Society. Cl, Br, or I), was very effective for a mild deoxygenative halogenation of Notice, though, that unlike the halogenation reactions above, conversion of an alcohol to a tosylate or mesylate proceeds with retention of configuration at the electrophilic carbon. Dehydroxylative Fluorination of Tertiary Alcohols. The resulting product is a vicinal (neighboring) dihalide. enables a convenient purification process, as the byproduct (EtO)3P═O and you may need to create a new Wiley Online Library account. Learn more. You have to login with your ACS ID befor you can login with your Mendeley account. Reaction Overview: The alkene halogenation reaction, specifically bromination or chlorination, is one in which a dihalide such as Cl2 or Br2 is added to a molecule after breaking the carbon to carbon double bond.The halides add to neighboring carbons from opposite faces of the molecule. Use the link below to share a full-text version of this article with your friends and colleagues. Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, China, Email: Unlimited viewing of the article/chapter PDF and any associated supplements and figures. The preparation of tert-butyl hypochlorite from tert-butyl alcohol is an example of electrophilic halogenation of oxygen, but this reaction is restricted to 3º-alcohols because 1º and 2º-hypochlorites lose HCl to give aldehydes and ketones. Changduo Pan, Chao Wu, Cheng Yuan, Jin-Tao Yu. You have to login with your ACS ID befor you can login with your Mendeley account. Dehydroxylative Trifluoromethylthiolation, Trifluoromethylation, and Difluoromethylation of Alcohols. http://pubs.acs.org/page/copyright/permissions.html. Recent Advances in Polychloromethylation Reactions. You’ve supercharged your research process with ACS and Mendeley!

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