Mesoions and ketene valence isomers.: Three types of rearrangement of mesoionic pyridopyrimidinylium olates involving ketene intermediates

被引：30

作者：

Fiksdahl, A ^{[1
]}

Plüg, C ^{[1
]}

Wentrup, C ^{[1
]}

机构：

[1] Univ Queensland, Dept Chem, Brisbane, Qld 4072, Australia

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2 | 2000年 / 09期

关键词：

D O I：

10.1039/b003662p

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The ketene valence isomers of mesoionic pyrimidinylium olates undergo (i) a retro-ene type fragmentation to C3O2 16 and 2-aminopyridine 15, (ii) an electrocyclisation to form a naphthyridine (19 --> 20 --> 21), or (iii) a cycloreversion to 2-pyridyl isocyanate 26 and a ketene 25.

引用

页码：1841 / 1845

页数：5

共 32 条

[1] INFRARED ABSORPTION SPECTRA OF CARBON SUBOXIDE AND MALONONITRILE IN SOLID ARGON MATRICES [J].

AMES, LL ;

WHITE, D ;

MANN, DE .

JOURNAL OF CHEMICAL PHYSICS, 1963, 38 (04) :910-&

[2] THE ABSORPTION SPECTRA OF THE AMINOPYRIDINES [J].

ANDERSON, LC ;

SEEGER, NV .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1949, 71 (01) :340-342

[3] Bimolecular kinetics at low temperatures using FTIR matrix isolation spectroscopy: Some caveats. Thermokinetic parameters for the reaction of fulvenones with pyridine in pyridine matrixes [J].

Andraos, J .

JOURNAL OF PHYSICAL CHEMISTRY A, 2000, 104 (07) :1532-1543

[4] DIRECT OBSERVATION OF BENZOYLKETENES [J].

ANDREICHIKOV, YS ;

KOLLENZ, G ;

KAPPE, CO ;

LEUNGTOUNG, R ;

WENTRUP, C .

ACTA CHEMICA SCANDINAVICA, 1992, 46 (07) :683-685

[5] AUTOMERIZATION OF A DEWAR THIOPHENE AND ITS EXO-S-OXIDE - DRAMATIC CONTRAST [J].

BUSHWELLER, CH ;

ROSS, JA ;

LEMAL, DM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1977, 99 (02) :629-631

[6]

CHAMBERS J, 1975, TETRAHEDRON LETT, P2783

[7]

COUTURIERTAMBUR.I, 2000, IN PRESS J PHYS CH A, V104

[8] 6-MEMBERED MESOIONIC HETEROCYCLES OF THE META-QUINODIMETHANE DIANION TYPE [J].

FRIEDRICHSEN, W ;

KAPPE, T ;

BOTTCHER, A .

HETEROCYCLES, 1982, 19 (06) :1083-1148

[9] VISIBLE LIGHT-INDUCED OXYGEN-TRANSFER FROM NITROGEN-DIOXIDE TO ETHYNE AND PROPYNE IN A CRYOGENIC MATRIX .1. IDENTIFICATION OF PRODUCTS [J].

HARRISON, JA ;

FREI, H .

JOURNAL OF PHYSICAL CHEMISTRY, 1994, 98 (47) :12142-12151

[10] VISCOSITY-DEPENDENT FLUORESCENCE AND LOW-TEMPERATURE PHOTOCHEMISTRY OF MESOIONIC 4-PHENYL-1,3,2-OXATHIAZOLYLIUM-5-OLATE [J].

HARRIT, N ;

HOLM, A ;

DUNKIN, IR ;

POLIAKOFF, M ;

TURNER, JJ .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1987, (09) :1227-1238

← 1 2 3 4 →