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Anwendungen der Phasentransfer‐Katalyse, 23. Notiz über Bromiodcarben und zugehörige Halogenaustausch‐prozesse
Author(s) -
V Dehmlow Eckehard,
Broda Witold
Publication year - 1982
Publication title -
chemische berichte
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.667
H-Index - 136
eISSN - 1099-0682
pISSN - 0009-2940
DOI - 10.1002/cber.19821151222
Subject(s) - chemistry , cyclopropane , nucleophile , halogen , alkene , medicinal chemistry , adduct , iodide , catalysis , salt (chemistry) , organic chemistry , ring (chemistry) , alkyl
Applications of Phase Transfer Catalysis, 23. Note on Bromoiodocarbene and on Pertinent Halogen Exchange Processes A rapid halogen exchange between HCBr 3 , HCBr 2 I, HCBrI 2 , and HCl 3 occurred in the presence of conc. sodium hydroxide and a quaternary ammonium salt. Trapping experiments with various alkenes give cyclopropane derivatives only in 3 cases. Depending on the nucleophilicity of the alkene and the haloform, different proportions of CBr 2 , CBrI, and Cl 2 adducts were obtained. The most nucleophilic acceptor trapped those carbenes preferentially that were formed by elimination of iodide.