Diels–Alder reactions of bicyclic, heteroannular dienones

1992 ◽  
Vol 70 (5) ◽  
pp. 1481-1485 ◽  
Author(s):  
Lucio Minuti ◽  
Roberta Selvaggi ◽  
Aldo Taticchi ◽  
Ming Guo ◽  
Ernest Wenkert
Keyword(s):  
Nmr Spectroscopy ◽  
Structure Analysis ◽  
Aluminum Chloride ◽  
Diels Alder ◽  
Face Selectivity

Aluminum chloride catalyzed Diels–Alder reactions of bicyclic dienones of the hexalone type with 1,3-butadiene, isoprene, (E)-piperylene, and (E)-1-methoxy-1,3-butadiene are described. Structure analysis of the adducts by NMR spectroscopy is presented. The site-, endo–exo-, and face-selectivity of the reactions are discussed.

Synthesis of perialkynylated tetrapyrazinoporphyrazines and its Optical Properties

2009 ◽  
Vol 2009 (5) ◽  
pp. 312-316 ◽  
Author(s):  
Chun Keun Jang ◽  
Jae Yun Jaung
Keyword(s):  
Optical Properties ◽  
Nmr Spectroscopy ◽  
Laser Desorption ◽  
Diels Alder ◽  
Visible Spectroscopy ◽  
H Nmr ◽  
Uv Visible ◽  
Tof Ms ◽  
Matrix Assisted Laser ◽  
Matrix Assisted Laser Desorption

Some phthalocyanines soluble in organic solvents have been developed by peripheral introduction of substituent groups. We report a new method for preparation of the polyphenyl-substituted dicyanopyrazines based on the [2 + 4] Diels-Alder cycloaddition of the tetraphenylcyclopentadienone to an ethynyl compound. The synthesised tetrapyrazinoporphyrazinato metal complexes were characterised by UV-visible spectroscopy, MALDI-TOF-Ms (matrix-assisted laser desorption ionisation time-of-flight mass) spectroscopy, and 1H NMR spectroscopy.

scholarly journals Synthesis and Diels–Alder cycloaddition reaction of norbornadiene and benzonorbornadiene dimers

2009 ◽  
Vol 5 ◽  
Author(s):  
Bilal Nişancı ◽  
Erdin Dalkılıç ◽  
Murat Güney ◽  
Arif Daştan
Keyword(s):  
Nmr Spectroscopy ◽  
Cycloaddition Reaction ◽  
Diels Alder

Dimeric forms of norbornadiene and benzonorbornadiene were synthesized starting with known monobromide derivatives. The Diels–Alder cycloaddition reaction of dimers with TCNE and PTAD was investigated and new norbornenoid polycyclics were obtained. All compounds were characterized properly using NMR spectroscopy.

Face selectivity in Diels-Alder reactions of chiral dienes containing allylic substituents

1988 ◽  
Vol 110 (14) ◽  
pp. 4625-4633 ◽  
Author(s):  
Matthew J. Fisher ◽  
Warren J. Hehre ◽  
Scott D. Kahn ◽  
Larry E. Overman
Keyword(s):  
Diels Alder ◽  
Face Selectivity

Oligophosphan-Liganden, XX [1] Reduktion von CO2 am Trisphosphanrhodium(I)-Komplex RhCl[t-BuP(CH2CH2CH2PMe2)2] Oligophosphine Ligands, X X [1] Reduction of Carbon Dioxide by the Trisphosphinerhodium (I) Complex RhCl[t-BuP(CH2CH2CH2PMe2)2]

1986 ◽  
Vol 41 (6) ◽  
pp. 718-721 ◽  
Author(s):  
Lutz Dahlenburg ◽  
Constanze Prengel ◽  
Nils Höck
Keyword(s):  
Carbon Dioxide ◽  
Nmr Spectroscopy ◽  
Structure Analysis ◽  
Nmr Spectra ◽  
X Ray

The reaction of Rh2Cl2(cyclo-C8H 12)2 with t-BuP(CH2CH2CH2PMe2)2 gave RhCl[t-BuP(CH2CH2CH2PMe2)2] (1) which was characterized by its 1H and 31P NMR spectra. 1 interacted with carbon dioxide to produce Rh(O2CO)Cl[t-BuP(CH2CH2CH2PMe2)2](2) and CO. 2 was studied by IR and 13C and 31P NMR spectroscopy as well as by an X-ray structure analysis. There is no evidence for any production of carbon dioxide derivatives containing C- or C- and O- bound integer CO2 ligands.

Influence of Lewis acids on the Diels–Alder reaction. III. Rearrangement of dimethyl N-carbomethoxy-7-azabicyclo[2.2.1]2,5-heptadiene-2,3-dicarboxylate adducts to dimethyl N-carbomethoxy-3-aminophthalates

1970 ◽  
Vol 48 (9) ◽  
pp. 1472-1474 ◽  
Author(s):  
R. C. Bansal ◽  
A. W. McCulloch ◽  
A. G. McInnes
Keyword(s):  
Aluminum Chloride ◽  
Lewis Acids ◽  
Alder Reaction ◽  
Diels Alder ◽  
Prolonged Treatment ◽  
Dimethyl Acetylenedicarboxylate ◽  
Diels Alder Reaction ◽  
Convenient Route

Aluminum chloride accelerates the Diels–Alder reactions of 2- or 2,5-substituted N-carbomethoxypyrroles with dimethyl acetylenedicarboxylate, and also catalyzes rearrangement of the N-carbomethoxy-7-azanorbornadiene adducts to 6- and 4,6-substituted dimethyl N-carbomethoxy-3-aminophthalates. Aromatization of the corresponding adduct of N-carbomethoxypyrrole only occurs on prolonged treatment with BF3. The procedure promises to be a convenient route for the synthesis of polysubstituted anilines.

Einfache Synthese von 2,2-Diethoxy-2,5-dihydrofuranen, 2(5 H)Furanonen und 2-Ethoxy-furanen.Kristall-und Molekülstruktur eines Barrelenon Diels-Aider Produktes [1] / Convenient Synthesis of 2,2-Diethoxy-2,5-dihydrofurans, 2(5 H)Furanones and 2-Ethoxyfurans.Crystal and Molecular Structure of a Barrelenone Diels-Alder Product [1]

1994 ◽  
Vol 49 (3) ◽  
pp. 389-406 ◽  
Author(s):  
Rolf W. Saalfrank ◽  
Wieland Hafner ◽  
Joachim Markmann ◽  
Andreas Welch ◽  
Karl Peters ◽  
...  
Keyword(s):  
Molecular Structure ◽  
Maleic Anhydride ◽  
Structure Analysis ◽  
Diels Alder ◽  
Dimethyl Acetylenedicarboxylate ◽  
Reaction Conditions ◽  
X Ray ◽  
Convenient Synthesis

AbstractReaction of 1,2-hydroxyketones 5 with (2,2-diethoxyvinylidene)triphenylphosphorane (2) or (2,2-diethoxyvinyl)triphenylphosphonium tetrafluoroborates 6 yields the 2,2-diethoxy- 2.5-dihydrofurans 9. Depending on the reaction conditions used, the orthoesters 9 can be hydrolized to give 2(5 H)furanones 10 and 2-ethoxyfurans 11, respectively. 4,5-Dimethyl- 5.6-dihydro-2-pyranone (20) and 8-methoxycoumarin (23) are prepared, starting from (2,2-diethoxyvinyl)triphenylphosphonium tetrafluoroborate (6 a) and 1-hydroxy-2-methyl- 3-butanone (16) or 2-hydroxy-3-methoxy-benzaldehyde (21). The 2-ethoxyfuranes 11 readily undergo Diels-Alder reactions with 2-chloracrylonitrile (24), maleic anhydride (26), N-phenyl-1,2,4-triazoline-3,5-dione (28) and dimethyl acetylenedicarboxylate (30) to give the corresponding Diels-Alder products 25, 27, 29 and 31, respectively. Contrary to 2-ethoxyfuran 11b , 11a reacts with two equivalents of acetylene 30, to yield barrelenone 34. The structure of 34 unequivocally is established by X-ray structure analysis.

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