SYNTHESIS AND SPIN-TRAPPING CHEMISTRY OF 5,5-DIMETHYL-2-(TRIFLUOROMETHYL)-1-PYRROLINE N-OXIDE

被引:24
作者
JANZEN, EG
ZHANG, YK
ARIMURA, M
机构
[1] OKLAHOMA MED RES FDN,FREE RAD BIOL & AGING RES PROGRAM,NATL BIOMED CTR SPIN TRAPPING & FREE RAD,OKLAHOMA CITY,OK 73104
[2] OKLAHOMA MED RES FDN,FREE RAD BIOL & AGING RES PROGRAM,OKLAHOMA MED RES FDN SPIN TRAP SOURCE,OKLAHOMA CITY,OK 73104
关键词
D O I
10.1021/jo00122a021
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A new five-membered ring nitrone, 5,5-dimethyl-2-(trifluoromethyl)-1-pyrroline N-oxide (2-TFDMPO), is synthesized for the purpose of spin trapping in free radical biology. Most of the spin adducts of 2-TFDMPO are persistent, and EPR, ENDOR, and MS spectra can be obtained. A variety of radicals give characteristic spectral signatures, among which is a rare type of line width alternation pattern due to hindered rotation of the trifluoromethyl group.
引用
收藏
页码:5434 / 5440
页数:7
相关论文
共 36 条
[1]  
[Anonymous], 2015, FREE RADICAL BIO MED
[2]   CHARACTERIZATION OF SPIN ADDUCTS OBTAINED WITH HYDROPHOBIC NITRONE SPIN TRAPS [J].
BARKER, P ;
BECKWITH, ALJ ;
CHERRY, WR ;
HUIE, R .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1985, (08) :1147-1150
[3]   DESIGNER SPIN TRAPS WITH A CYCLIC NITRONE STRUCTURE [J].
DEHNEL, A ;
GRILLER, D ;
KANABUSKAMINSKA, JM .
JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (07) :1566-1567
[4]   READILY ACCESSIBLE 12-I-5 OXIDANT FOR THE CONVERSION OF PRIMARY AND SECONDARY ALCOHOLS TO ALDEHYDES AND KETONES [J].
DESS, DB ;
MARTIN, JC .
JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (22) :4155-4156
[5]   THE 1ST H-1 AND N-14 ENDOR SPECTRA OF AN OXYGEN-CENTERED RADICAL ADDUCT OF DMPO-TYPE NITRONES [J].
HAIRE, DL ;
OEHLER, UM ;
GOLDMAN, HD ;
DUDLEY, RL ;
JANZEN, EG .
CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1988, 66 (09) :2395-2402
[6]   A MORE EFFICIENT SYNTHESIS OF DMPO-TYPE (NITRONE) SPIN TRAPS [J].
HAIRE, DL ;
HILBORN, JW ;
JANZEN, EG .
JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (22) :4298-4300
[7]   SYNTHESIS AND CHARACTERIZATION OF PHENYL-SUBSTITUTED C-PHENYL-N-TERT-BUTYLNITRONES AND SOME OF THEIR RADICAL ADDUCTS [J].
HINTON, RD ;
JANZEN, EG .
JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (09) :2646-2651
[8]   CRITICAL EXAMINATION OF FLUORINE HYPERCONJUGATION IN AROMATIC SYSTEMS [J].
HOLTZ, D .
CHEMICAL REVIEWS, 1971, 71 (01) :139-&
[9]  
IWAHASHI H, 1992, ANAL CHEM, V64, P224
[10]   ENDOR SPECTRA OF AMINOXYLS - CONFORMATIONAL STUDY OF ALKYL AND ARYL SPIN ADDUCTS OF DEUTERATED ALPHA-PHENYL-N-TERT-BUTYLNITRONE (PBN) BASED ON PROTON AND BETA-C-13 HYPERFINE SPLITTINGS [J].
JANZEN, EG ;
OEHLER, UM ;
HAIRE, DL ;
KOTAKE, Y .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (22) :6858-6863