MARKED NORMAL SALT EFFECTS ON STEREOSELECTIVITY OF RING-OPENING OF AN ARYLOXIRANE IN ACID-MEDIA

被引:24
作者
BATTISTINI, C [1 ]
CROTTI, P [1 ]
FERRETTI, M [1 ]
MACCHIA, F [1 ]
机构
[1] UNIV PISA,IST CHIM ORGAN & CHIM FARMACEUT,I-56100 PISA,ITALY
关键词
D O I
10.1021/jo00445a017
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:4067 / 4071
页数:5
相关论文
共 36 条
[1]   STERIC INHIBITION OF RESONANCE AND REGIOSELECTIVITY AND STEREOSELECTIVITY IN RING-OPENING OF 1-ARYL-SUBSTITUTED EPOXIDES - REACTIONS OF 1-PHENYL-2,2-DIMETHYL-7-OXABICYCLO[4.1.0]HEPTANE UNDER ACIDIC CONDITIONS [J].
BALSAMO, A ;
CROTTI, P ;
MACCHIA, B ;
MACCHIA, F .
TETRAHEDRON, 1973, 29 (01) :199-204
[2]   CONJUGATIVE AND INDUCTIVE EFFECTS IN RING-OPENING OF 1-ARYL SUBSTITUTED OXIRANES - SOME REACTIONS OF 1-( PARA METHOXYPHENYL)-1,2-EPOXYCYCLOHEXANES AND 1-(META METHOXYPHENYL)-1,2-EPOXYCYCLOHEXANES UNDER ACIDIC CONDITIONS [J].
BALSAMO, A ;
CROTTI, P ;
MACCHIA, B ;
MACCHIA, F .
TETRAHEDRON, 1973, 29 (14) :2183-2188
[3]  
BALSAMO A, 1976, GAZZ CHIM ITAL, V106, P77
[4]   CRITICAL DEPENDENCE OF STABILITY OF AN OVERCROWDED BENZYLIC CARBOCATION ON AROMATIC RING SUBSTITUENT - SUBSTITUENT AND SOLVENT EFFECTS ON RING-OPENING OF 1-ARYL-SUBSTITUTED EPOXIDES - 1-(P-METHOXYPHENYL)-2,2-DIMETHYL-7-OXABICYCLO[4.1.0]HEPTANE [J].
BALSAMO, A ;
CROTTI, P ;
MACCHIA, B ;
MACCHIA, F .
JOURNAL OF ORGANIC CHEMISTRY, 1974, 39 (07) :874-877
[5]   Mechanism of substitution at a saturated carbon atom - Part XXII - A kinetic demonstration of the unimolecular solvolysis of alkyl halides - (Section D) Kinetics of, and salt effects in, the hydrolysis of pp '-dimethylbenzhydryl chloride in aqueous acetone [J].
Bateman, LC ;
Hughes, ED ;
Ingold, CK .
JOURNAL OF THE CHEMICAL SOCIETY, 1940, :974-978
[6]   Mechanism of substitution at a saturated carbon atom - Part XXIII - A kinetic demonstration of the unimolecular solvolysis of alkyl halides - (Section E) A general discussion [J].
Bateman, LC ;
Church, MG ;
Hughes, ED ;
Ingold, CK ;
Taher, NA .
JOURNAL OF THE CHEMICAL SOCIETY, 1940, :979-1011
[7]  
BATISTINI C, 1977, TETRAHEDRON, V33, P1629
[8]  
BATTISTINI A, 1974, J CHEM SOC CHEM COMM, P712
[9]  
BATTISTINI C, 1977, GAZZ CHIM ITAL, V107, P153
[10]  
BATTISTINI C, 1975, TETRAHEDRON LETT, P2091