THE UNUSUALLY SLOW HYDROLYSIS RATE OF SILYL METHYL KETALS IN BENZOQUINONE SYSTEMS - THE QUESTION OF SILOXY STABILIZATION OF AN ADJACENT POSITIVE CHARGE AND STEREOELECTRONIC EFFECTS ON KETAL HYDROLYSIS

被引:27
作者
STERN, AJ [1 ]
SWENTON, JS [1 ]
机构
[1] OHIO STATE UNIV,DEPT CHEM,COLUMBUS,OH 43210
关键词
D O I
10.1021/jo00273a033
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
引用
收藏
页码:2953 / 2958
页数:6
相关论文
共 26 条
[1]   PROBING THE ANOMERIC EFFECT - TRIMETHYLSILYLOXY AND TERT-BUTOXY SUBSTITUENTS IN 1,4-DIOXANE DERIVATIVES - THEORY VS EXPERIMENT [J].
APED, P ;
APELOIG, Y ;
ELLENCWEIG, A ;
FUCHS, B ;
GOLDBERG, I ;
KARNI, M ;
TARTAKOVSKY, E .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (05) :1486-1495
[2]   A MECHANISTIC STUDY OF THE THERMAL DISPROPORTIONATION REACTION OF QUINONE MONOKETALS [J].
CAPPARELLI, MP ;
SWENTON, JS .
JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (24) :5360-5364
[3]  
Colvin E. W., 1981, SILICON ORGANIC SYNT
[4]   ORGANOSILICON COMPOUNDS .8. THE (TRIMETHYLSILYLMETHYL)BENZOIC ACIDS [J].
EABORN, C ;
PARKER, SH .
JOURNAL OF THE CHEMICAL SOCIETY, 1954, (MAR) :939-941
[5]  
Fritz JS., 1979, QUANTITATIVE ANAL CH
[6]   RAPID-INJECTION NUCLEAR-MAGNETIC-RESONANCE INVESTIGATION OF THE REACTIVITY OF ALPHA-ALKOXY AND BETA-ALKOXY KETONES WITH DIMETHYLMAGNESIUM - KINETIC EVIDENCE FOR CHELATION [J].
FRYE, SV ;
ELIEL, EL ;
CLOUX, R .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (06) :1862-1863
[7]   PREVENTION OF CHELATION BY AN OXYGEN FUNCTION THROUGH PROTECTION WITH A TRIISOPROPYL SILYL GROUP [J].
FRYE, SV ;
ELIEL, EL .
TETRAHEDRON LETTERS, 1986, 27 (28) :3223-3226
[8]  
Hanstein W., 1970, J AM CHEM SOC, V92, P829
[9]  
HENTON DR, 1980, J ORG CHEM, V45, P3422, DOI 10.1021/jo01305a010
[10]   THE EFFECT OF PROTECTING GROUPS ON CHELATION CONTROL [J].
KAHN, SD ;
KECK, GE ;
HEHRE, WJ .
TETRAHEDRON LETTERS, 1987, 28 (03) :279-280