Diels–Alder reaction of furan and fumaryl chloride: X-ray crystal and molecular structure of an oxabicyclo[2.2.1]heptane derivative. Synthesis of reduction products of cis-maneonene-A

Author(s):  
Clive L. D. Jennings-White ◽  
Andrew B. Holmes ◽  
Paul R. Raithby
ChemInform ◽  
2010 ◽  
Vol 29 (51) ◽  
pp. no-no
Author(s):  
V. V. PLEMENKOV ◽  
S. V. RUL' ◽  
A. T. GUBAIDULLIN ◽  
I. A. LITVINOV ◽  
I. P. KARASEVA ◽  
...  

2006 ◽  
Vol 61 (4) ◽  
pp. 385-395 ◽  
Author(s):  
Gerhard Maas ◽  
Robert Reinhard ◽  
Hans-Georg Herz

2-Aminodienes, in which the enamine function is incorporated in a five-, six-, or seven-membered ring, react with dimethyl acetylenedicarboxylate in a sequence of [2+2] cycloaddition and electrocyclic ring-opening to form the two-carbon ring expanded unsaturated heterocycles, i.e., 3,4- dicarboxylate substituted 6,7-dihydro-1H-azepines 3, 8 and 21, 1,6,7,8-tetrahydroazocines 22, and 6,7,8,9-tetrahydro-1H-azonines 13. Similarly, 2-[(2-thienyl)ethynyl]-4,5,6,7-tetrahydro-1H-azepine 9 is converted into 2-[(2-thienyl)ethynyl]-6,7,8,9-1H-azonine-3,4-dicarboxylate 10 which was characterized by X-ray structure determination. The eight- and nine-membered azaheterocycles 22 and 13, which have not been isolated, undergo thermal isomerization at elevated temperatures. Thus, ring contraction by a 6π-electrocyclic reaction takes place for N-methyl substituted azonine 13, while the N-allyl moiety of azocines 22 engages in an intramolecular Diels-Alder reaction or a 1,7- electrocyclization reaction


ChemInform ◽  
2010 ◽  
Vol 23 (44) ◽  
pp. no-no
Author(s):  
T. IBATA ◽  
Y. ISOGAMI ◽  
H. NAKAWA ◽  
H. TAMURA ◽  
H. SUGA ◽  
...  

1989 ◽  
Vol 42 (11) ◽  
pp. 1869 ◽  
Author(s):  
HD Becker ◽  
BW Skelton ◽  
AH White

The molecular structures of ethyl di-9-anthrylglycolate (1) and methyl di-9-anthrylglycolate (2), as well as those of three isomerization products of (2), have been established by single-crystal X-ray diffraction studies. In both (1) and (2), the anthracenemoieties are characterized by marked deviations from planarity. The stereospecific course of the thermal and photochemical isomerization of (2) by Diels -Alder reaction is suggested to be governed by the spatial demand of the alkoxycarbonyl group. Base-catalysed isomerization of (2) by migration of 9-anthryl from carbon to oxygen is associated with steric relief.


Heterocycles ◽  
1998 ◽  
Vol 47 (2) ◽  
pp. 793 ◽  
Author(s):  
Naomichi Furukawa ◽  
Shao-Zhong Zhang ◽  
Ernst Horn ◽  
Ohgi Takahashi ◽  
Soichi Sato ◽  
...  

2013 ◽  
Vol 28 (4) ◽  
pp. 307-311 ◽  
Author(s):  
M.A. Macías ◽  
J.A. Henao ◽  
Arnold R. Romero Bohórquez ◽  
Vladimir V. Kouznetsov

The 2,4-diaryl 1,2,3,4-tetrahydroquinoline derivative (1), described in the title (Chemical formula: C23H22N2O3), was synthesized via the “one-pot” three-component imino Diels–Alder reaction catalyzed by Cu(OTf)2. Molecular characterization was performed by 1H and 13C NMR, Fourier transform-infrared, and gas chromatography-mass spectrometry. The X-ray powder diffraction pattern for the title compound was analyzed and found to be crystallized in an orthorhombic system with space group P212121 (No. 19) and refined unit-cell parameters a = 8.6415(8) Å, b = 12.679(2) Å, c = 17.601(2) Å, and V = 1928.4(2) Å3.


1992 ◽  
Vol 70 (7) ◽  
pp. 2040-2045 ◽  
Author(s):  
Alan R. Katritzky ◽  
Irina V. Shcherbakova ◽  
Robert D. Tack ◽  
Peter J. Steel

Reactions of N-formylmorpholine/POCl3 with several unactivated olefins yield the corresponding α,β-unsaturated aldehydes. Norbornene affords with dimethylformamide/POCl3 a product formed by a novel inverse-electron demand Diels–Alder reaction of an acyclic 2-azoniodiene. The structure of this product was confirmed by X-ray analysis. Crystals are monoclinic: a = 8.025(3), b = 11.670(3), c = 9.309(4) Å, β = 108.03(3)°, P21, Z = 2; the structure was refined to R = 0.044 for 1379 independent observed reflections.


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