ACID-CATALYZED HYDRATION OF DI-TERT-BUTYLKETENE

被引:31
作者
KABIR, SH
SEIKALY, HR
TIDWELL, TT
机构
[1] UNIV TORONTO,DEPT CHEM,TORONTO M5S 1A1,ONTARIO,CANADA
[2] UNIV TORONTO,SCARBOROUGH COLL,W HILL M1C 1A0,W HILL,CANADA
关键词
D O I
10.1021/ja00498a059
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
We report new evidence relevant to the mechanism of ketene hydration. Specifically di-tert-butylketene (1) undergoes hydration to the acid 2 in 50% water-acetonitrile with general acid catalysis and a solvent isotope effect kH+/kD+ of 2.8. These facts indicate that the reaction occurs by rate-limiting proton transfer. © 1979, American Chemical Society. All rights reserved.
引用
收藏
页码:1059 / 1060
页数:2
相关论文
共 27 条
[1]  
AUSLOOS P, 1977, CHEM PHYS LETT, V51, P33
[2]   ACIDITY FUNCTIONS OF SOME AQUEOUS ACIDS [J].
BASCOMBE, KN ;
BELL, RP .
JOURNAL OF THE CHEMICAL SOCIETY, 1959, (MAR) :1096-1105
[3]   REACTIONS OF KETEN .3. KINETICS OF SPONTANEOUS AND ACETIC ACID-CATALYZED REACTIONS OF KETEN WITH WATER [J].
BLAKE, PG ;
DAVIES, HH .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1972, (03) :321-&
[4]   RATE OF ACID FORMATION FROM PHENYLKETENES IN AQUEOUS-SOLUTION [J].
BOTHE, E ;
MEIER, H ;
SCHULTEFROHLINDE, D ;
SONNTAG, CV .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1976, 15 (06) :380-381
[5]   HALOGENATED KETENES .29. FURTHER-STUDIES ON MIXED DIMERIZATIONS [J].
BRADY, WT ;
TING, PL .
JOURNAL OF ORGANIC CHEMISTRY, 1976, 41 (13) :2336-2339
[6]  
CHERKASOVA EM, 1977, USP KHIM+, V46, P477
[7]  
CHIANG Y, UNPUBLISHED
[8]   RATES OF ACID-CATALYZED HYDRATION OF ISOMERIC Z-E ALKENES - EFFECTS OF STERIC CROWDING ON ADDITIONS TO ALKENES [J].
CHWANG, WK ;
TIDWELL, TT .
JOURNAL OF ORGANIC CHEMISTRY, 1978, 43 (10) :1904-1908
[9]   GAS-PHASE DISSOCIATION OF PROTONATED ACETIC-ACID TO ACYL CATION AND WATER - HEAT OF FORMATION OF CH3CO+ AND PROTON AFFINITY OF KETENE [J].
DAVIDSON, WR ;
LAU, YK ;
KEBARLE, P .
CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1978, 56 (07) :1016-1019
[10]   KETENE-ION CHEMISTRY AND PROTON AFFINITY [J].
DEBROU, GB ;
FULFORD, JE ;
LEWARS, EG ;
MARCH, RE .
INTERNATIONAL JOURNAL OF MASS SPECTROMETRY AND ION PROCESSES, 1978, 26 (04) :345-352