EXPERIMENTAL-EVIDENCE FOR A SYNPERIPLANAR STEREOELECTRONIC EFFECT IN THE OZONOLYSIS OF A TRICYCLIC ACETAL

被引:30
作者
LI, SG [1 ]
DESLONGCHAMPS, P [1 ]
机构
[1] UNIV SHERBROOKE,FAC SCI,DEPT CHIM,SYNTHESE ORGAN LAB,SHERBROOKE J1K 2R1,QUEBEC,CANADA
关键词
D O I
10.1016/S0040-4039(00)61559-9
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Tricyclic acetal 1 in which the ring oxygen has one electron pair synperiplanar to the C-H bond is easily oxidized with ozone.
引用
收藏
页码:7759 / 7762
页数:4
相关论文
共 12 条
[1]   OZONOLYSIS OF ACETALS - (1) ESTER SYNTHESIS, (2) THP ETHER CLEAVAGE, (3) SELECTIVE OXIDATION OF BETA-GLYCOSIDE, (4) OXIDATIVE REMOVAL OF BENZYLIDENE AND ETHYLIDENE PROTECTING GROUPS [J].
DESLONGC.P ;
MOREAU, C .
CANADIAN JOURNAL OF CHEMISTRY, 1971, 49 (14) :2465-&
[2]   IMPORTANCE OF CONFORMATION IN OZONOLYSIS OF ACETALS [J].
DESLONGC.P ;
ATLANI, P ;
FREHEL, D ;
MOREAU, C .
CANADIAN JOURNAL OF CHEMISTRY, 1972, 50 (20) :3402-&
[3]   OXIDATION OF ACETALS BY OZONE [J].
DESLONGCHAMPS, P ;
ATLANI, P ;
FREHEL, D ;
MALAVAL, A ;
MOREAU, C .
CANADIAN JOURNAL OF CHEMISTRY, 1974, 52 (21) :3651-3664
[4]  
DESLONGCHAMPS P, 1983, ORGANIC CHEM SERIES, V1, P41
[5]   THE ANOMERIC AND REVERSE ANOMERIC EFFECT - A SIMPLE ENERGY DECOMPOSITION MODEL FOR ACETALS AND PROTONATED ACETALS [J].
GREIN, F ;
DESLONGCHAMPS, P .
CANADIAN JOURNAL OF CHEMISTRY, 1992, 70 (05) :1562-1572
[6]   ON THE NATURE OF THE ANOMERIC EFFECT IN XHN-CH2-OH SYSTEMS, WITH X = F, O, N, C [J].
GREIN, F ;
DESLONGCHAMPS, P .
CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1992, 70 (02) :604-611
[7]  
GRENIN F, IN PRESS ACS MONOGRA
[8]   STEREOELECTRONIC ASPECTS OF THE ANOMERIC EFFECT IN FLUOROMETHYLAMINE [J].
IRWIN, JJ ;
HA, TK ;
DUNITZ, JD .
HELVETICA CHIMICA ACTA, 1990, 73 (07) :1805-1817
[9]   SOLVATION EFFECTS ON CONFORMATIONAL EQUILIBRIA . STUDIES RELATED TO CONFORMATIONAL PROPERTIES OF 2-METHOXYTETRAHYDROPYRAN AND RELATED METHYL GLYCOPYRANOSIDES [J].
LEMIEUX, RU ;
PAVIA, AA ;
MARTIN, JC ;
WATANABE, KA .
CANADIAN JOURNAL OF CHEMISTRY, 1969, 47 (23) :4427-&
[10]   ALPHA,ALPHA' ANNELATION OF CYCLIC KETONES - SYNTHESIS AND CONFORMATIONAL PROPERTIES OF BICYCLO[3.3.1]NONANONE DERIVATIVES [J].
MCEUEN, JM ;
NELSON, RP ;
LAWTON, RG .
JOURNAL OF ORGANIC CHEMISTRY, 1970, 35 (03) :690-+