Reactivity of glucosyl radical in the presence of phenols

被引:15
作者
Alberti, A
DellaBona, MA
Macciantelli, D
Pelizzoni, F
Sello, G
Torri, G
Vismara, E
机构
[1] UNIV MILAN,DIPARTIMENTO CHIM ORGAN & IND,I-20133 MILAN,ITALY
[2] IST GIULIANA RONZONI,I-20133 MILAN,ITALY
[3] DIPARTIMENTO CHIM POLITECN,I-20131 MILAN,ITALY
关键词
D O I
10.1016/0040-4020(96)00558-3
中图分类号
O62 [有机化学];
学科分类号
070303 [有机化学]; 081704 [应用化学];
摘要
Glucosyl radicals from the photoreaction of alpha-bromo-2,3,4,6-tetra-O-acetylglucose (ABG) with hexabutylditin react with phenols. 4-H3COC6H4O. was identified by means of EPR spectroscopy in the case of 4-methoxyphenol, and the corresponding alpha-O-glucoside was isolated along with 1- and 2-deoxysugars and the dimers of glucosyl radical. The present results are consistent with the formation of alpha-O-glucosides observed in the electrochemical reaction of ABG and phenols, although in this case the dimers represent the main reaction products. Copyright (C) 1996 Published by Elsevier Science Ltd
引用
收藏
页码:10241 / 10248
页数:8
相关论文
共 15 条
[1]
AN ESR APPROACH TO HYPERVALENT IODINE INDUCED IODODECARBOXYLATION [J].
ALBERTI, A ;
BENAGLIA, M ;
VISMARA, E .
RESEARCH ON CHEMICAL INTERMEDIATES, 1989, 11 (02) :117-126
[2]
[Anonymous], 1973, ORGANIC ELECTROCHEMI
[3]
Benedetto M, 1995, CARBOHYDR LETT, V1, P321
[4]
AUTOXIDATION OF BIOLOGICAL MOLECULES .4. MAXIMIZING THE ANTIOXIDANT ACTIVITY OF PHENOLS [J].
BURTON, GW ;
DOBA, T ;
GABE, EJ ;
HUGHES, L ;
LEE, FL ;
PRASAD, L ;
INGOLD, KU .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (24) :7053-7065
[5]
AUTHENTIC STANDARDS FOR THE REDUCTIVE-CLEAVAGE METHOD - THE POSITIONAL ISOMERS OF PARTIALLY METHYLATED AND ACETYLATED OR BENZOYLATED 1,5-ANHYDRO-D-GLUCITOL [J].
ELVEBAK, LE ;
GRAY, GR .
CARBOHYDRATE RESEARCH, 1995, 274 :85-97
[6]
Giese B., 1990, ORG SYNTH, V69, P66
[7]
Giese B., 1986, RADICALS ORGANIC SYN
[8]
ELECTRON-SPIN RESONANCE STUDIES .33. EVIDENCE FOR HETEROLYTIC AND HOMOLYTIC TRANSFORMATIONS OF RADICALS FROM 1,2-DIOLS AND RELATED COMPOUNDS [J].
GILBERT, BC ;
NORMAN, ROC ;
LARKIN, JP .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1972, (06) :794-&
[9]
ELECTRON-SPIN RESONANCE SPECTROSCOPIC INVESTIGATION OF CARBOHYDRATE RADICALS .4. 1,2-ACYLOXYL MIGRATION IN PYRANOSYL RADICALS [J].
KORTH, HG ;
SUSTMANN, R ;
GRONINGER, KS ;
LEISUNG, M ;
GIESE, B .
JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (18) :4364-4369
[10]
CLEAVAGE OF TIN-CARBON BONDS OF ORGANOSILYLSTANNANE AND ORGANODISTANNANE IN PHOTOINDUCED ELECTRON-TRANSFER REACTIONS AND MASS-SPECTROMETRY [J].
KYUSHIN, S ;
OTANI, S ;
NAKADAIRA, Y ;
OHASHI, M .
CHEMISTRY LETTERS, 1995, (01) :29-30