Reactivity of ketenes in matrices. Direct observation of ketene-pyridine ylides

被引:62
作者
Qiao, GGH [1 ]
Andraos, J [1 ]
Wentrup, C [1 ]
机构
[1] JAMES COOK UNIV N QUEENSLAND,DEPT CHEM,BRISBANE,QLD 4072,AUSTRALIA
关键词
D O I
10.1021/ja9607190
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Ketenes 7, 14, and 17 have been generated in pyridine matrices and observed by infrared spectroscopy to react with pyridine at temperatures between 15 and 50 K to form ketene-pyridine ylides 12, 15, and 18. Azaheterocyclic ketenes 20, 23, and 26 dimerize or tetramerize at ca. 50 K, whereby one ketene molecule acts as a nucleophile toward the other, forming a transient ketene-imine ylide.
引用
收藏
页码:5634 / 5638
页数:5
相关论文
共 44 条
[1]   NUCLEAR MAGNETIC-RESONANCE STUDIES .7. C-13 AND N-15 NMR OF DIAZO-COMPOUNDS [J].
ALBRIGHT, TA ;
FREEMAN, WJ .
ORGANIC MAGNETIC RESONANCE, 1977, 9 (02) :75-79
[2]   DIRECT OBSERVATION AND REACTIVITY OF TRANSIENT KETENES GENERATED BY FLASH-PHOTOLYSIS [J].
ALLEN, AD ;
ANDRAOS, J ;
KRESGE, AJ ;
MCALLISTER, MA ;
TIDWELL, TT .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (05) :1878-1879
[3]   KINETIC AND THEORETICAL-STUDIES OF RING-CLOSURE OF UNSTABILIZED BISKETENES TO CYCLOBUTENEDIONES [J].
ALLEN, AD ;
COLOMVAKOS, JD ;
EGLE, I ;
LUSZTYK, J ;
MCALLISTER, MA ;
TIDWELL, TT ;
WAGNER, BD ;
ZHAO, DC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (28) :7552-7553
[4]   HYDRATION OF BIS(PENTAMETHYLPHENYL)KETENE AND BISMESITYLKETENE LEADING TO ENE-1,1-DIOLS (ENOLS OF CARBOXYLIC-ACIDS) [J].
ALLEN, BM ;
HEGARTY, AF ;
ONEILL, P ;
NGUYEN, MT .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1992, (06) :927-934
[5]   THE STRUCTURE OF SOME DIAZOPHENOLS [J].
ANDERSON, LC ;
ROEDEL, MJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1945, 67 (06) :955-958
[6]   THE MECHANISM OF THE REACTION OF DIPHENYLKETENE WITH BASES IN AQUEOUS-SOLUTION - NUCLEOPHILIC-ATTACK VERSUS GENERAL BASE CATALYSIS OF KETENE HYDRATION [J].
ANDRAOS, J ;
KRESGE, AJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (14) :5643-5646
[7]   FLASH PHOTOLYTIC GENERATION AND STUDY OF KETENE AND CARBOXYLIC-ACID ENOL INTERMEDIATES FORMED BY THE PHOTOLYSIS OF DIAZONAPHTHOQUINONES IN AQUEOUS-SOLUTION [J].
ANDRAOS, J ;
CHIANG, Y ;
HUANG, CG ;
KRESGE, AJ ;
SCAIANO, JC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (23) :10605-10610
[8]   ON THE PHOTODECOMPOSITION MECHANISM OF ORTHO-DIAZONAPHTHOQUINONES [J].
BARRA, M ;
FISHER, TA ;
CERNIGLIARO, GJ ;
SINTA, R ;
SCAIANO, JC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (07) :2630-2634
[9]   CONDENSED CYCLOBUTANE AROMATIC SYSTEMS .5. THE SYNTHESIS OF SOME ALPHA-DIAZOINDANONES - RING CONTRACTION IN THE INDANE SERIES [J].
CAVA, MP ;
LITLE, RL ;
NAPIER, DR .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1958, 80 (09) :2257-2263
[10]   A SEMIEMPIRICAL THEORETICAL-STUDY ON THE FORMATION OF BETA-LACTAMS FROM KETENES AND IMINES [J].
COSSIO, FP ;
UGALDE, JM ;
LOPEZ, X ;
LECEA, B ;
PALOMO, C .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (03) :995-1004