The Use of Bromotrichloromethane in Chlorination Reactions

被引：30
|
作者：
Newman, Stephen G. [1 ]
Bryan, Christopher S. [1 ]
Perez, Didier [1 ]
Lautens, Mark [1 ]
机构：
[1] Univ Toronto, Dept Chem, Toronto, ON M5S 3H6, Canada
来源：
SYNTHESIS-STUTTGART | 2011年 / 02期
基金：
加拿大自然科学与工程研究理事会;
关键词：
olefination; aldehydes; halogenation; Appel reaction; benzyl halides; STEREOSELECTIVE-SYNTHESIS; TRISUBSTITUTED ALKENES; SELECTIVE SYNTHESIS; VINYL DICHLORIDES; INTERNAL ALKYNES; 1,1-DICHLORO-1-ALKENES; 1,1-DIBROMO-1-ALKENES; KETONES; ALDEHYDES; TRIPHENYLPHOSPHINE;
D O I：
10.1055/s-0030-1258368
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Carbon tetrachloride is no longer used as a common solvent due to its toxicity and harmful environmental impact. The synthesis of gem-dichloroalkenes from aldehydes by using triphenylphosphine typically requires carbon tetrachloride as a solvent. We report that stoichiometric bromotrichloromethane in acetonitrile can be used in place of solvent quantities of carbon tetrachloride in this transformation. Similarly, bromotrichloromethane in dichloromethane can be used for the room-temperature Appel reaction of benzyl alcohols to form benzyl chlorides, which is commonly carried out in refluxing carbon tetrachloride.
引用
收藏
页码：342 / 346
页数：5
相关论文
共 50 条
  • [21] LIGNIN REACTIONS UNDER ACID CHLORINATION
    SUNDHOLM, L
    SVENSK PAPPERSTIDNING-NORDISK CELLULOSA, 1969, 72 (02): : 46 - &
  • [22] REACTIONS OF ATOMS AND FREE RADICALS IN SOLUTION .11. THE ADDITION OF BROMOTRICHLOROMETHANE TO OLEFINS
    KHARASCH, MS
    REINMUTH, O
    URRY, WH
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1947, 69 (05) : 1105 - 1110
  • [23] Kinetics and degradation mechanism of Benzophenone-3 in chlorination and UV/chlorination reactions
    Lee, Young-Min
    Lee, Gowoon
    Kim, Moon-Kyung
    Zoh, Kyung-Duk
    CHEMICAL ENGINEERING JOURNAL, 2020, 393
  • [24] BENZYLIC BROMINATION WITH BROMOTRICHLOROMETHANE
    BALDWIN, SW
    ONEILL, TH
    SYNTHETIC COMMUNICATIONS, 1976, 6 (02) : 109 - 112
  • [25] Use of N-chloro-N-methyl-p-toluenesulfonamide in N-chlorination reactions
    Pastoriza, Cristina
    Manuel Antelo, Juan
    Crugeiras, Juan
    JOURNAL OF PHYSICAL ORGANIC CHEMISTRY, 2013, 26 (07) : 551 - 559
  • [26] USE AND COST OF CHLORINATION SYSTEMS
    KASPER, JR
    CHOW, W
    GRAHAM, J
    MUSSALLI, YG
    POWER ENGINEERING, 1983, 87 (10) : 54 - 57
  • [27] Use of chlorination for chromite upgrading
    Kanari, N
    Gaballah, I
    Allain, E
    THERMOCHIMICA ACTA, 2000, 351 (1-2) : 109 - 117
  • [28] INVESTIGATIONS OF THE STRUCTURE AND REACTIONS OF THE INTERMEDIATE IN THE CHLORINATION OF RESORCINOL
    HEASLEY, VL
    ANDERSON, ME
    COMBES, DS
    ELIAS, DS
    GARDNER, JT
    HERNANDEZ, ML
    MORELAND, RJ
    SHELLHAMER, DF
    ENVIRONMENTAL TOXICOLOGY AND CHEMISTRY, 1993, 12 (09) : 1653 - 1659
  • [29] Kinetics of elementary reactions in the chain chlorination of cyclopropane
    Hurley, MD
    Schneider, WF
    Wallington, TJ
    Mann, DJ
    DeSain, JD
    Taatjes, CA
    JOURNAL OF PHYSICAL CHEMISTRY A, 2003, 107 (12): : 2003 - 2010
  • [30] USE OF BROMOTRICHLOROMETHANE TO PROBE INTO GLOW-DISCHARGE POLYMERIZATION OF PROPYLENE AND EHTYLENE
    SHARMA, AK
    MILLICH, F
    HELLMUTH, EW
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1978, 176 (SEP): : 79 - 79
12345