Photochemistry of N-acetyl and N-benzoyl carbazoles: photo-Fries rearrangement and photoinduced single electron transfer

被引:28
作者
Bonesi, SM [1 ]
Erra-Balsells, R [1 ]
机构
[1] Univ Buenos Aires, Fac Ciencias Exactas & Nat, Dept Quim Organ, RA-1430 Buenos Aires, DF, Argentina
关键词
N-acyl carbazole; N-acetyl carbazole; N-benzoyl carbazole; photo-Fries; photo-rearrangement; photoinduced single electron transfer (PSET);
D O I
10.1016/S1010-6030(97)00126-3
中图分类号
O64 [物理化学(理论化学)、化学物理学];
学科分类号
070304 ; 081704 ;
摘要
The photochemistry of two N-acyl carbazoles, N-acetyl and N-benzoyl carbazole, in different pure and mixed organic solvents is studied. Depending on the properties of the medium, photo-Fries rearrangement and photoinduced single electron transfer (PSET) processes are observed yielding the former I-acyl and 3-acyl carbazoles and the latter 3-chloro-N-acyl carbazole. k(SV), k(Q) and phi for fluorescence emission, conversion of N-acyl carbazole and product formation yields have been measured as well as the properties of the N-acyl carbazole radical cations formed during the PSET process (laser flash photolysis experiments). The Rehm-Weller equation is used in order to evaluate the Delta G degrees(ET) of the PSET processes. (C) 1997 Elsevier Science S.A.
引用
收藏
页码:271 / 284
页数:14
相关论文
共 36 条
  • [11] PRODUCT STUDY OF THE PHOTOLYSIS OF N-ACETYL CARBAZOLE IN ETHANOL AND DICHLOROMETHANE SOLUTION .1.
    BONESI, SM
    ERRABALSELLS, R
    [J]. JOURNAL OF PHOTOCHEMISTRY AND PHOTOBIOLOGY A-CHEMISTRY, 1991, 56 (01) : 55 - 72
  • [12] On the synthesis and isolation of chlorocarbazoles obtained by chlorination of N-substituted carbazoles
    Bonesi, SM
    ErraBalsells, R
    [J]. JOURNAL OF HETEROCYCLIC CHEMISTRY, 1997, 34 (03) : 891 - 900
  • [13] BONESI SM, 1991, AN ASOC QUIM ARGENT, V79, P113
  • [14] RECENT WORK ON THE SYNTHESIS OF 3,6-DIBENZOYLCARBAZOLE
    BONESI, SM
    ERRABALSELLS, R
    [J]. JOURNAL OF HETEROCYCLIC CHEMISTRY, 1991, 28 (04) : 1035 - 1038
  • [15] BONESI SM, 1995, THESIS U BUENOS AIRE
  • [16] PHOTO-FRIES REARRANGEMENTS IN N-SULFONYL CARBAZOLES
    CHAKRABARTI, A
    BISWAS, GK
    CHAKRABORTY, DP
    [J]. TETRAHEDRON, 1989, 45 (16) : 5059 - 5064
  • [17] ERRABALSELLS R, 1984, TETRAHEDRON LETT, V25, P5363
  • [18] ERRABALSELLS R, 1985, AN ASOC QUIM ARGENT, V73, P207
  • [19] FOX MA, 1988, PHOTOINDUCED ELECT A
  • [20] Frasca A. R., 1983, TETRAHEDRON, V39, P33