The reaction of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) with carbon dioxide

被引:309
作者
Heldebrant, DJ
Jessop, PG
Thomas, CA
Eckert, CA
Liotta, CL
机构
[1] Queens Univ, Dept Chem, Kingston, ON K7L 3N6, Canada
[2] Georgia Inst Technol, Sch Chem, Atlanta, GA 30332 USA
[3] Georgia Inst Technol, Sch Chem Engn, Atlanta, GA 30332 USA
关键词
D O I
10.1021/jo0503759
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Amidines have been reported to react with CO2 to form a stable and isolable zwitterionic adduct but previous studies were performed in the presence of at least some water. However, spectroscopy of the reaction between DBU and CO2 detects the rapid formation of the bicarbonate salt of DBU when wet DBU is exposed to CO2 and does not indicate that an isolable zwitterionic adduct between DBU and CO2 forms either in the presence or the absence of water. © 2005 American Chemical Society.
引用
收藏
页码:5335 / 5338
页数:4
相关论文
共 22 条
  • [1] Reaction of ketenylidenetriphenylphosphorane, Ph3PC=C=O, with water:: formation of methyltriphenylphosphonium hydrogencarbonate
    Benetollo, F
    Bertani, R
    Ganis, P
    Pace, G
    Pandolfo, L
    Zanotto, L
    [J]. JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2002, 642 (1-2) : 64 - 70
  • [2] INFRARED SPECTRA OF ISOTOPIC BICARBONATE MONOMER IONS
    BERNITT, DL
    HARTMAN, KO
    HISATSUNE, IC
    [J]. JOURNAL OF CHEMICAL PHYSICS, 1965, 42 (10) : 3553 - +
  • [3] Superbase catalysis of oxazolidin-2-one ring formation from carbon dioxide and prop-2-yn-1-amines under homogeneous or heterogenous conditions
    Costa, M
    Chiusoli, GP
    Taffurelli, D
    Dalmonego, G
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1998, (09): : 1541 - 1546
  • [4] Carboxylation and mitsunobu reaction of amines to give carbamates: Retention vs inversion of configuration is substituent-dependent
    Dinsmore, CJ
    Mercer, SP
    [J]. ORGANIC LETTERS, 2004, 6 (17) : 2885 - 2888
  • [5] A novel construction of a reversible fixation-release system of carbon dioxide by amidines and their polymers
    Endo, T
    Nagai, D
    Monma, T
    Yamaguchi, H
    Ochiai, B
    [J]. MACROMOLECULES, 2004, 37 (06) : 2007 - 2009
  • [6] CARBOXYLATION OF ACTIVE METHYLENE COMPOUNDS USING REAGENT OF 1,8-DIAZABICYCLO (5.4.0)-7-UNDECENE AND CARBON-DIOXIDE
    HARUKI, E
    ARAKAWA, M
    MATSUMURA, N
    OTSUJI, Y
    IMOTO, E
    [J]. CHEMISTRY LETTERS, 1974, (05) : 427 - 428
  • [7] Haruki E., 1982, ORGANIC SYNTHESES CA, P5
  • [8] Iwatani M., 1978, SEKIYU GAKKAISHI, V21, P290
  • [9] Amine-catalyzed, one-pot coproduction of dialkyl carbonates and 1,2-diols from epoxides, alcohols, and carbon dioxide
    Kishimoto, Y
    Ogawa, I
    [J]. INDUSTRIAL & ENGINEERING CHEMISTRY RESEARCH, 2004, 43 (26) : 8155 - 8162
  • [10] PALLADIUM-CATALYZED GENERATION OF O-ALLYLIC URETHANES AND CARBONATES FROM AMINES/ALCOHOLS, CARBON-DIOXIDE, AND ALLYLIC CHLORIDES
    MCGHEE, WD
    RILEY, DP
    CHRIST, ME
    CHRIST, KM
    [J]. ORGANOMETALLICS, 1993, 12 (04) : 1429 - 1433