ACID-CATALYZED HYDROLYSIS OF CYCLIC BENZOPHENONE ACETALS - EFFECTS OF RING SIZE AND RING SUBSTITUENT

被引:6
作者
OSHIMA, T
UENO, SY
NAGAI, T
机构
[1] Institute of Chemistry, College of General Education, Osaka University, Toyonaka, Osaka
关键词
D O I
10.3987/COM-94-S48
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Rates of acid-catalyzed hydrolysis of 5- to 8-membered ring benzophenone acetals (1-4) in 80% dioxane-water(v/v) were dependent upon the ring size and the ring-substituted methyl group as well as the condensed-rings. These kinetic results are interpreted in terms of the ring strain, the stereoelectronic effects, and the hydrophobicity.
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页码:607 / 617
页数:11
相关论文
共 14 条
[1]  
BERGSTROM RG, 1980, CHEM ETHERS CROWN ET
[2]  
CEDER O, 1954, ARK KEMI, V6, P523
[3]   MECHANISM AND CATALYSIS FOR HYDROLYSIS OF ACETALS, KETALS, AND ORTHO-ESTERS [J].
CORDES, EH ;
BULL, HG .
CHEMICAL REVIEWS, 1974, 74 (05) :581-603
[4]  
CORDES EH, 1967, PROGR PHYS ORG CHEM, V4, P1
[5]  
Deslongchamps P., 1983, STEREOELECTRONIC EFF
[7]  
FIFE TH, 1975, ADV PHYS ORG CHEM, V11, P1
[8]   HYDROLYSIS OF SUBSTITUTED CROWN ETHER ACETALS [J].
OSHIMA, T ;
NAGAI, T .
JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (06) :1465-1468
[9]  
OSHIMA T, 1980, TETRAHEDRON LETT, P3319
[10]  
SCHMITZ E, 1967, CHEM ETHER LINKAGE