Mechanistic Investigation of the Oxidative Cleavage of the Carbon-Carbon Double Bond in α,β-Unsaturated Compounds by Hexachloroiridate(IV) in Acetate Buffer

2013 ◽  
Vol 46 (1) ◽  
pp. 31-40 ◽  
Author(s):  
Biswajit Pal
Keyword(s):  
Double Bond ◽  
Oxidative Cleavage ◽  
Acetate Buffer ◽  
Unsaturated Compounds ◽  
Carbon Double Bond ◽  
Mechanistic Investigation

Preparation of New Oxidized 18-α-Oleanane Derivatives

2005 ◽  
Vol 70 (9) ◽  
pp. 1447-1464 ◽  
Author(s):  
Miroslav Kvasnica ◽  
Iva Tišlerová ◽  
Jan Šarek ◽  
Jan Sejbal ◽  
Ivana Císařová
Keyword(s):  
Double Bond ◽  
Nmr Spectra ◽  
Biological Activities ◽  
Oxidative Cleavage ◽  
Allylic Oxidation ◽  
Unsaturated Ketone ◽  
Ruthenium Tetroxide ◽  
Unsaturated Compounds ◽  
Starting Compound ◽  
C Nmr

19β,28-Epoxy-4,5-seco-3,5-cyclo-18α-olean-3(5)-ene (2) is an appropriate compound for oxidations, which lead to new oxidized compounds with potential biological activities. Several oxidations were used such as epoxidation, allylic oxidation, oxidative cleavage of double bond and other ones. From the starting compound epoxides 3a, 3b and unsaturated ketone 4 were prepared. This ketone was further oxidized to diketone 6 and anhydride 7. The double bonds of all unsaturated compounds were cleaved with ruthenium tetroxide to afford new A-seco oleananes. The structure and stereochemistry of the compounds were derived from IR, MS, 1H and 13C NMR spectra (1D and 2D COSY, TOCSY, NOESY, HSQC, HMBC).

Copper-Catalyzed Oxidative Cleavage of Carbon—Carbon Double Bond of Enol Ethers with Molecular Oxygen.

ChemInform ◽  
2006 ◽  
Vol 37 (11) ◽  
Author(s):  
Makoto Tokunaga ◽  
Yuki Shirogane ◽  
Hiroshi Aoyama ◽  
Yasushi Obora ◽  
Yasushi Tsuji
Keyword(s):  
Double Bond ◽  
Molecular Oxygen ◽  
Oxidative Cleavage ◽  
Enol Ethers ◽  
Carbon Double Bond

Copper-catalyzed oxidative cleavage of carbon–carbon double bond of enol ethers with molecular oxygen

2005 ◽  
Vol 690 (23) ◽  
pp. 5378-5382 ◽  
Author(s):  
Makoto Tokunaga ◽  
Yuki Shirogane ◽  
Hiroshi Aoyama ◽  
Yasushi Obora ◽  
Yasushi Tsuji
Keyword(s):  
Double Bond ◽  
Molecular Oxygen ◽  
Oxidative Cleavage ◽  
Enol Ethers ◽  
Carbon Double Bond

Aerobic oxidative cleavage of C=C double bond of styrene catalyzed by simple manganese porphyrin

2006 ◽  
Vol 10 (07) ◽  
pp. 942-947 ◽  
Author(s):  
Yong-Fei Li ◽  
Can-Cheng Guo ◽  
Xu-Hui Yan ◽  
Qiang Liu
Keyword(s):  
Double Bond ◽  
Reaction Temperature ◽  
Styrene Oxide ◽  
Product Distribution ◽  
Oxidative Cleavage ◽  
Double Bonds ◽  
Manganese Porphyrin ◽  
Carbon Double Bond ◽  
Air System ◽  
Styrene Conversion

The aerobic oxidative cleavage of styrene C=C double bonds catalyzed by simple manganese porphyrin is reported. Under the catalysis of chloro(tetraphenylporphinato)manganese, the oxidative cleavage of the carbon-carbon double bond of the styrene with air yields benzaldehyde. Our results show that the oxidative cleavage and the epoxidation of the styrene double bond are the competition reactions in the styrene-manganese porphyrin-air system. The reaction temperature decided the product distribution. Under the conditions of 0.4 MPa air and 30 ppm of chloro(tetraphenylporphinato)manganese, the styrene conversion was 20.0% and the selectivity of benzaldehyde and styrene oxide was 81.7% and 12.7% respectively when the reaction temperature was 110°C. Styrene conversion was 92.5% and the selectivity of benzaldehyde and styrene oxide was 48.1% and 41.2% respectively when the reaction temperature was 120°C.

Novel cobalt(II)-catalyzed oxidative cleavage of a carbon-carbon double bond

1986 ◽  
Vol 108 (9) ◽  
pp. 2453-2454 ◽  
Author(s):  
R. S. Drago ◽  
B. B. Corden ◽  
C. W. Barnes
Keyword(s):  
Double Bond ◽  
Oxidative Cleavage ◽  
Carbon Double Bond

Reactions of 4-Pyrones with Azomethine Ylides as a Chemo­selective Method for the Construction of Multisubstituted Pyrano[2,3-c]pyrrolidines

Synthesis ◽  
2021 ◽  
Author(s):  
Dmitrii L. Obydennov ◽  
Vyacheslav D. Steben’kov ◽  
Konstantin L. Obydennov ◽  
Sergey A. Usachev ◽  
Vladimir S. Moshkin ◽  
...  
Keyword(s):  
Double Bond ◽  
Ring Opening ◽  
Azomethine Ylides ◽  
Azomethine Ylide ◽  
Dipolar Cycloaddition ◽  
Computational Studies ◽  
Carbon Double Bond ◽  
Reactivity Indexes ◽  
Reaction Proceeds

Abstract4-Pyrones bearing electron-donating and electron-withdrawing groups react with nonstabilized azomethine ylides to form pyrano[2,3-c]pyrrolidines in moderate to good yields. The reaction proceeds chemoselectively as a 1,3-dipolar cycloaddition of the azomethine ylide at the carbon–carbon double bond of the pyrone activated by the electron-withdrawing substituent. The reactivity of 4-pyrones toward azomethine ylides was rationalized by computational studies with the use of reactivity indexes. The pyrano[2,3-c]pyrrolidine moiety could be modified, for example by a ring-opening transformation under the action of hydrazine to provide pyrazolyl-substituted pyrrolidines.

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