Photoinduced decarboxylation reactions -: Radical chemistry in water

被引:63
作者
Griesbeck, AG [1 ]
Kramer, W [1 ]
Oelgemöller, M [1 ]
机构
[1] Univ Cologne, Inst Organ Chem, D-50939 Cologne, Germany
关键词
D O I
10.1039/a905076k
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Intramolecular photodecarboxylation reactions of potassium omega-phthalimido carboxylates in water or mixtures of water and organic solvents (acetone, acetonitrile) were investigated using an incoherent XeCl excimer radiation source emitting at 308 nm. Electron transfer induced intermolecular addition of alkyl carboxylates to phthalimides likewise proceeded efficiently under these conditions. The reactions can be performed in multigram (i.e. 10-30 g product) quantities using easiliy available substrates such as glutamic acid (for the synthesis of 3), leucine (for 8, 9) or simple alkyl carboxylates (for 11). The advantages of this methodology are: clean and high-yielding reactions, solvent and waste minimization, water-based processes and efficient utilization of photons of defined energy.
引用
收藏
页码:205 / 207
页数:3
相关论文
共 14 条
  • [1] UV EXCIMER RADIATION FROM DIELECTRIC-BARRIER DISCHARGES
    ELIASSON, B
    KOGELSCHATZ, U
    [J]. APPLIED PHYSICS B-PHOTOPHYSICS AND LASER CHEMISTRY, 1988, 46 (04): : 299 - 303
  • [2] Griesbeck A. G., UNPUB
  • [3] GRIESBECK AG, 1994, SYNLETT, P931
  • [4] PHOTO-ELECTRON TRANSFER INDUCED MACROCYCLIZATION OF N-PHTHALOYL-OMEGA-AMINOCARBOXYLIC ACIDS
    GRIESBECK, AG
    HENZ, A
    PETERS, K
    PETERS, EM
    VONSCHNERING, HG
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1995, 34 (04): : 474 - 476
  • [5] Decarboxylative photocyclization: Synthesis of benzopyrrolizidines and macrocyclic lactones
    Griesbeck, AG
    Nerowski, F
    Lex, J
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (14) : 5213 - 5217
  • [6] Griesbeck AG, 1996, LIEBIGS ANN, P1951
  • [7] Griesbeck AG, 1998, CHIMIA, V52, P272
  • [8] Synthesis of medium- and large-ring compounds initiated by photochemical decarboxylation of omega-phthalimidoalkanoates
    Griesbeck, AG
    Henz, A
    Kramer, W
    Lex, J
    Nerowski, F
    Oelgemoller, M
    Peters, K
    Peters, EM
    [J]. HELVETICA CHIMICA ACTA, 1997, 80 (03) : 912 - 933
  • [9] Griesbeck AG, 1999, SYNLETT, P492
  • [10] Stereoselective Yang cyclizations of α-amido ketones
    Griesbeck, AG
    Heckroth, H
    Lex, J
    [J]. CHEMICAL COMMUNICATIONS, 1999, (12) : 1109 - 1110