Ring Opening and C(ω)-S Coupling: Nickel-Mediated Transformation of Alicyclic Alkoxyhydroperoxides

被引：0
|
作者：
Fomenkov, Dmitri I. [1 ]
Budekhin, Roman A. [1 ]
Mulina, Olga M. [1 ]
Komarova, Olga A. [1 ]
Doronin, Mikhail M. [1 ]
Belyakova, Yulia Yu. [1 ]
He, Liang-Nian [2 ,3 ]
Yaremenko, Ivan A. [1 ]
Terent'ev, Alexander O. [1 ]
机构：
[1] Russian Acad Sci, N D Zelinsky Inst Organ Chem, 47 Leninsky prosp, Moscow 119991, Russia
[2] Nankai Univ, State Key Lab, Tianjin 300071, Peoples R China
[3] Nankai Univ, Inst Elemento Organ Chem, Coll Chem, Tianjin 300071, Peoples R China
来源：
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2025年 / 28卷 / 07期
基金：
俄罗斯科学基金会;
关键词：
<italic>ozonolysis</italic>; <italic>peroxide</italic>; <italic>radicals</italic>; <italic>beta-scission</italic>; <italic>nickel</italic>; OZONOLYSIS; MECHANISMS; METAL; CONVENIENT; RADICALS;
D O I：
10.1002/ejoc.202401198
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Ozonolysis of cycloalkanone semicarbazones in alcohol containing solution with the subsequent addition of nickel (II) dithiocarbamates or xanthates was found to result in omega-xanthyl or omega-dithiocarbamyl carboxylic acid esters. The reaction proceeds in several steps. The initial one is cycloalkanone semicarbazone ozonolysis in the presence of alcohol, which leads to alicyclic alkoxyhydroperoxide. The second step is an extraordinary interaction between the alkoxyhydroperoxide and nickel (II) dithiocarbamate or xanthate, which proceeds via alkoxy radical formation and its subsequent beta-scission, resulting in C-S coupling products. The developed method allows to obtain omega-xanthyl or omega-dithiocarbamyl esters in yields up to 52 % relative to the initial cycloalkanone semicarbazone.
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页数：7
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