70372-58-6Relevant articles and documents
TMSCFX2(X = Cl, Br) as halofluorocarbene sources for the synthesis of halofluorocyclopropanes
Chen, Dingben,Fan, Zili,Huang, Ling,Gao, Kaili,Xiao, Pan,Ni, Chuanfa,Hu, Jinbo
supporting information, p. 319 - 322 (2021/01/25)
TMSCFX2 (X = Cl, Br; TMS = trimethylsilyl) have been developed as halofluorocarbene (CFX, X = Cl, Br) precursors for [2+1] cyclopropanation with alkenes. Structurally diverse halofluorocyclopropanes were obtained in good to excellent yields. It was found
(NHC)AgCl catalyzed bromofluorocyclopropanation of alkenes with CFBr2CO2Na
Andrianova, Anastasia A.,Maslova, Yulia D.,Novikov, Maxim A.,Semenov, Sergei E.,Nefedov, Oleg M.
, p. 49 - 55 (2018/03/08)
An effective method for bromofluorocyclopropanation of electron-rich (aryl substituted), electron-neutral (monoalkyl substituted), electron-poor (haloalkenes, allylic esters, α,β-unsaturated esters) and acid/base sensitive silyl- and boronyl substituted a
Copper-catalyzed ligand free ring-opening amination of gem-fluorohalocyclopropanes – An efficient route toward 2-fluoroallylamines
Novikov, Maxim A.,Ibatov, Yaroslav A.,Volchkov, Nikolai V.,Lipkind, Maria B.,Semenov, Sergei E.,Nefedov, Oleg M.
supporting information, p. 58 - 72 (2017/01/18)
Ring-opening amination of gem-chlorofluoro- and gem-bromofluorocyclopropanes with secondary alkyl, aryl amines or hydroxylamines catalyzed by copper(I) or copper(II) compounds with no additional ligands affords tertiary 2-fluoroallylamines or hydroxylamines in moderate to excellent yields. The reaction pathway involves isomerization of gem-fluorohalocyclopropanes to 2-fluoroallyl halides followed by in situ nucleophilic substitution of a halide by an N-nucleophile. The p-methoxyphenyl (PMP) protective group is efficient in the preparation of secondary 2-fluoroallylamines by this method. Primary 2-fluoroallylamines can only be obtained by a stepwise protocol including CuX-catalyzed isomerization of gem-fluorohalocyclopropanes to 2-fluoroallylic halides followed by amination.
Copper(I)-catalyzed solvolysis of gem-chlorofluoro- and gem-bromofluorocyclopropanes. Preparation of 2-fluoroallylic ethers, esters and alcohols
Novikov, Maxim A.,Volchkov, Nikolai V.,Lipkind, Maria B.,Nefedov, Oleg M.
, p. 131 - 143 (2015/10/05)
Copper(I)-catalyzed solvolysis of gem-chlorofluoro- and gem-bromofluorocyclopropanes in MeOH, NaOAc/AcOH, NaOAc/DMF, HCO2Na/HCO2H or water/dioxane affords 2-fluoroallylic ethers, esters or alcohols in moderate to excellent yields. Th
Three-component heterocyclization of gem -bromofluorocyclopropanes with NOBF4: Access to 4-fluoropyrimidine N -oxides
Sedenkova, Kseniya N.,Averina, Elena B.,Grishin, Yuri K.,Kutateladze, Andrei G.,Rybakov, Victor B.,Kuznetsova, Tamara S.,Zefirov, Nikolay S.
, p. 9893 - 9899 (2013/01/15)
Novel three-component heterocyclization involving gem- bromofluorocyclopropanes, nitrosyl tetrafluoroborate, and a molecule of the solvent (nitrile) yielding previously unknown fluorinated pyrimidine N-oxides is described. A two-step synthetic approach to 4-fluoropyrimidine N-oxides from alkenes under mild conditions is developed using this reaction. Mechanistic aspects of the heterocyclization are discussed.
Substituent Effects in the Solvolysis of p-(2-Substituted Cyclopropyl)-α-Methylbenzyl Chlorides
Kusuyama, Yoshiaki,Kubo, Takako,Iyo, Masami,Kagosaku, Tamami,Tokami, Kenjiro
, p. 2954 - 2960 (2007/10/02)
The solvolysis rates of p-(cis- or trans-2-substituted cyclopropyl)-α-methylbenzyl chlorides including electron-donating and electron-attracting substituents relative to a hydrogen substituent were measured in 80percent aqueous acetone.The trans isomers w
