Revisiting the reaction of hydroxyl radicals with vicinal diols in water

被引:12
|
作者
Jiang, Dong [1 ]
Barata-Vallejo, Sebastian [2 ]
Golding, Bernard T. [1 ]
Ferreri, Carla [2 ]
Chatgilialoglu, Chryssostomos [2 ]
机构
[1] Newcastle Univ, Sch Chem, Newcastle Upon Tyne NE1 7RU, Tyne & Wear, England
[2] CNR, ISOF, I-40129 Bologna, Italy
关键词
AQUEOUS-SOLUTION; REARRANGEMENTS; ANTIOXIDANTS; MECHANISMS; GLYCOL;
D O I
10.1039/c1ob06538f
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The carbonyl products of the reactions of hydroxyl radicals with three vicinal diols (ethane-1,2-diol, propane-1,2-diol and butane-2,3-diol) have been identified and quantified. Hydroxyl radicals were produced by gamma-radiolysis of N2O-saturated aqueous solutions. The reactions result in the formation of alkoxyl radicals (similar to 15%) followed by beta-fragmentation, and alpha-hydroxyl alkyl radicals that undergo H2O elimination. The latter process is part of a radical chain reaction at higher diol concentrations.
引用
下载
收藏
页码:1102 / 1107
页数:6
相关论文
共 50 条
  • [41] REACTION OF OXYGEN WITH POLYNUCLEOTIDES FOLLOWING ATTACK BY HYDROXYL RADICALS
    MICHAELS, HB
    HUNT, JW
    RADIATION RESEARCH, 1974, 59 (01) : 192 - 192
  • [42] Kinetics and mechanism of the reaction of recombination of vinyl and hydroxyl radicals
    Knyazev, Vadim D.
    CHEMICAL PHYSICS LETTERS, 2017, 685 : 165 - 170
  • [43] CLEAVAGE OF VICINAL DIOLS BY PYRIDINIUM CHLOROCHROMATE
    CISNEROS, A
    FERNANDEZ, S
    HERNANDEZ, JE
    SYNTHETIC COMMUNICATIONS, 1982, 12 (11) : 833 - 838
  • [44] Radical deoxygenation of alcohols and vicinal diols with N-ethylpiperidine hypophosphite in water
    Jang, DO
    Cho, DH
    TETRAHEDRON LETTERS, 2002, 43 (34) : 5921 - 5924
  • [45] Diastereoselective Synthesis of Vicinal Tertiary Diols
    Loertscher, Brad M.
    Young, Phil R.
    Evans, Patrick R.
    Castle, Steven L.
    ORGANIC LETTERS, 2013, 15 (08) : 1930 - 1933
  • [46] A NEW METHOD FOR DEOXYGENATION OF VICINAL DIOLS
    BARUA, NC
    SHARMA, RP
    TETRAHEDRON LETTERS, 1982, 23 (13) : 1365 - 1366
  • [47] PREPARATION OF MONOSILYL ETHERS OF VICINAL DIOLS
    ANTONSEN, O
    BENNECHE, T
    UNDHEIM, K
    ACTA CHEMICA SCANDINAVICA, 1992, 46 (08): : 757 - 760
  • [48] Unprecedented copper(I)-catalyzed photochemical reaction of diethyl ether with vicinal diols and ketals
    Mondal, Sujit
    Yadav, Ram Naresh
    Ghosh, Subrata
    TETRAHEDRON LETTERS, 2010, 51 (33) : 4452 - 4454
  • [49] DIRECT STEREOSPECIFIC CONVERSION OF ACYCLIC VICINAL DIOLS INTO OLEFINS AND ITS REACTION-MECHANISM
    OHRUI, H
    NAGIHASHI, K
    MEGURO, H
    BIOSCIENCE BIOTECHNOLOGY AND BIOCHEMISTRY, 1992, 56 (11) : 1721 - 1724
  • [50] Capture of Hydroxyl Radicals by Hydronium Cations in Water Microdroplets
    Xing, Dong
    Meng, Yifan
    Yuan, Xu
    Jin, Shuihui
    Song, Xiaowei
    Zare, Richard N.
    Zhang, Xinxing
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2022, 61 (33)