A NOVEL AND CONVENIENT APPROACH TO FUNCTIONALIZED 2,6,9-TRIOXABICYCLO[3.3.1]NONA-3,7-DIENES (BRIDGED BIS-DIOXINES)

被引：30
作者：
KAPPE, CO
FARBER, G
WENTRUP, C
KOLLENZ, G
机构：
[1] KARL FRANZENS UNIV GRAZ,INST ORGAN CHEM,A-8010 GRAZ,AUSTRIA
[2] KARL FRANZENS UNIV GRAZ,INST PHYS CHEM,A-8010 GRAZ,AUSTRIA
来源：
TETRAHEDRON LETTERS | 1992年 / 33卷 / 32期
关键词：
D O I：
10.1016/S0040-4039(00)61310-2
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The synthesis of N-aryl-2,6,9-trioxabicycloE3.3.1]nona-3,7-diene-4-carboxamides 2 by reaction of dipivaloylketene-dimer 1 with aromatic amines is described. Bis-derivatives 5, 6 resp. are formed from 1 and aromatic diamines. The structure of N-phenylcarboxamide 2a was proved by X-ray crystallography, the chirality of these compounds (e.g. 2b) established by NMR studies. A reasonable reaction pathway for the unusual transformation 1 --> 2 is discussed, too.
引用
收藏
页码：4553 / 4556
页数：4
相关论文
共 7 条
[1]   2,6,9-TRIOXABICYCLO[3.3.1]NONA-3,7-DIENE-4,8-DICARBALDEHYDE, A DISSYMMETRIC PROPELLER-LIKE MOLECULE - THE STRUCTURE AND CHIRALITY PROOF [J].
ARNOLD, Z ;
BUDESINSKY, M .
JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (22) :5352-5353
[2]   ISOLATION, CHARACTERIZATION AND RESOLUTION OF 1,3,5,7-TETRAMETHYL-2,6,9-TRIOXO-BICYCLO[3.3.1]NONA-3,7-DIENE [J].
DERENZI, A ;
PANUNZI, A ;
PAOLILLO, L ;
VITAGLIANO, A .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1977, 124 (02) :221-228
[3]   STRUCTURE OF A DIOLEFINE COMPLEX OF PLATINUM(2) C10H14O3PTCL2 [J].
GIBSON, D ;
OLDHAM, C ;
LEWIS, J ;
LAWTON, D ;
MASON, R ;
ROBERTSO.GB .
NATURE, 1965, 208 (5010) :580-&
[4]   METAL BETA-DIKETONE COMPLEXES .4. ACID DERIVATIVES OF SOME PLATINUM-CARBON BONDED ACETYLACETONE COMPLEXES [J].
GIBSON, D ;
LEWIS, J ;
OLDHAM, C .
JOURNAL OF THE CHEMICAL SOCIETY A -INORGANIC PHYSICAL THEORETICAL, 1967, (01) :72-&
[5]   DIPIVALOYLKETENE AND ITS UNUSUAL DIMERIZATION TO A PERMANENTLY STABLE ALPHA-OXOKETENE [J].
KAPPE, CO ;
EVANS, RA ;
KENNARD, CHL ;
WENTRUP, C .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (11) :4234-4237
[6]   CRYSTAL STRUCTURE OF A DIOLEFIN COMPLEX OF PLATINUM(2) [J].
MASON, R ;
ROBERTSON, GB .
JOURNAL OF THE CHEMICAL SOCIETY A -INORGANIC PHYSICAL THEORETICAL, 1969, (03) :492-+
[7]   STRUCTURE OF 2,6,9-TRIOXABICYCLO[3.3.1]NONA-3,7-DIENE-4,8-DICARBALDEHYDE [J].
PODLAHA, J ;
PODLAHOVA, J ;
ARNOLD, Z ;
MALY, K ;
PETRICEK, V .
ACTA CRYSTALLOGRAPHICA SECTION C-STRUCTURAL CHEMISTRY, 1988, 44 :1966-1968
1