endo/exo isomerism in norcarane and 2-norcaranol hydrotrioxides (ROOOH)

被引:12
作者
Erzen, E [1 ]
Cerkovnik, J [1 ]
Plesnicar, B [1 ]
机构
[1] Univ Ljubljana, Fac Chem & Chem Technol, Dept Chem, Ljubljana 1000, Slovenia
关键词
D O I
10.1021/jo035154m
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Ozonation of norcarane (1) yielded endo and exo norcarane hydrotrioxides (2a, 2b), as characterized by H-1 and C-13 NMR spectroscopy. Further ozonation of the primary decomposition products of these hydrotrioxides, i.e., 2-norcaranols (3), produced the corresponding isomeric 2-norcaranol hydrotrioxides (4a, 4b), and hydrogen trioxide (HOOOH).
引用
收藏
页码:9129 / 9131
页数:3
相关论文
共 25 条
[1]   Revisiting the mechanism of P450 enzymes with the radical clocks norcarane and spiro[2,5]octane [J].
Auclair, K ;
Hu, ZB ;
Little, DM ;
de Montellano, PRO ;
Groves, JT .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (21) :6020-6027
[2]   Magnesium promoted cyclopropanation reactions of allylic alcohols [J].
Bolm, C ;
Pupowicz, D .
TETRAHEDRON LETTERS, 1997, 38 (42) :7349-7352
[3]   Evidence for HOOO radicals in the formation of alkyl hydrotrioxides (ROOOH) and hydrogen trioxide (HOOOH) in the ozonation of C-H bonds in hydrocarbons [J].
Cerkovnik, J ;
Erzen, E ;
Koller, J ;
Plesnicar, B .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (03) :404-409
[4]   PREPARATION OF CYCLIC CYCLOPROPYLCARBINOLS [J].
DAUBEN, WG ;
BEREZIN, GH .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1963, 85 (04) :468-&
[5]   ORGANIC PEROXIDES .1. THE PREPARATION OF ALKYL HYDROPEROXIDES FROM HYDROGEN PEROXIDE [J].
DAVIES, AG ;
FOSTER, RV ;
WHITE, AM .
JOURNAL OF THE CHEMICAL SOCIETY, 1953, (MAY) :1541-1547
[6]   BONDING PROPERTIES OF CYCLOPROPANE AND THEIR CHEMICAL CONSEQUENCES [J].
DEMEIJERE, A .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1979, 18 (11) :809-826
[7]  
DEMEIJERE A, 1988, ORG PEROXOVERBINDU E, V13, P971
[8]   TITANIUM(IV) CHLORIDE CATALYZED CYCLOPROPANATIONS OF ALKENES USING ZINC DUST, COPPER(I) CHLORIDE, AND DIHALOMETHANES [J].
FRIEDRICH, EC ;
LUNETTA, SE ;
LEWIS, EJ .
JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (10) :2388-2390
[9]   KINETICS OF OZONATION .6. POLYCYCLIC ALIPHATIC-HYDROCARBONS [J].
GIAMALVA, DH ;
CHURCH, DF ;
PRYOR, WA .
JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (15) :3429-3432
[10]   KINETICS OF OZONATION .5. REACTIONS OF OZONE WITH CARBON-HYDROGEN BONDS [J].
GIAMALVA, DH ;
CHURCH, DF ;
PRYOR, WA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (24) :7678-7681