The oxidation of 2-alkoxy-3,6-di-tert-butylphenols.: The reversible dimerization of 2-alkoxy-3,6-di-tert-butylphenoxy radicals

被引:18
作者
Abakumov, GA [1 ]
Cherkasov, VK [1 ]
Nevodchikov, VI [1 ]
Druzhkov, NO [1 ]
Fukin, GK [1 ]
Kursky, YA [1 ]
Piskunov, AV [1 ]
机构
[1] GA Razuvaev Inst Organomet Chem, Nizhnii Novgorod 603950, Russia
基金
俄罗斯基础研究基金会;
关键词
phenol; oxidation; phenoxy radical; reversible dissociation;
D O I
10.1016/j.tetlet.2005.04.012
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The oxidation of 2-alkoxy-3,6-di-tert-butylphenols has been studied. It was found that 2-RO-3,6-di-tert-butylphenoxy radicals (R = Et, Pr, Ph) undergo dimerization by C-O coupling. The X-ray structure of 2-ethoxy-3,6-di-tert-butylphenoxy dimer has been determined. Radical dimers dissociate reversibly in solution to give two phenoxy radicals at 200-350 K. By using EPR spectroscopy the equilibrium concentration of the phenoxy radicals, equilibrium constants and AH and AS of dissociation have been determined. (c) 2005 Elsevier Ltd. All rights reserved.
引用
收藏
页码:4095 / 4097
页数:3
相关论文
共 5 条
[1]   REACTION ON THE ADDITION OF SOME ORGANOMETALLIC COMPOUNDS TO 3,6-DI-TERT-BUTYL-O-BENZOQUINONE - NEW O-QUINONES [J].
ABAKUMOV, GA ;
CHERKASOV, VK ;
ABAKUMOVA, LG ;
NEVODCHIKOV, VI ;
DRUZHKOV, NO ;
MAKARENKO, NP ;
KURSKY, JA .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1995, 491 (1-2) :127-133
[2]  
BELOSTOCKAYA IS, 1973, B ACAD SCI USSR CH, P2808
[3]  
PROKOFEVA TI, 1985, B ACAD SCI USSR CH, P1324
[4]  
PROKOFIEV AI, 1978, DOKL AKAD NAUK SSSR+, V239, P1367
[5]   NUCLEAR MAGNETIC RESONANCE STUDIES OF A RADICAL-RADICAL DIMERIZATION REACTION [J].
WILLIAMS, DJ ;
KREILICK, R .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1967, 89 (14) :3408-&