Partially fluorinated heterocyclic compounds. Part 16. Preparation of furan derivatives from pentafluorophenyl and heptafluoro-2-naphthyl prop-2-ynyl ethers with aromatic compounds, and the isolation of hydrogen-abstraction products

Author(s):  
Gerald M. Brooke
1977 ◽  
Vol 165 (2) ◽  
pp. 395-402 ◽  
Author(s):  
J Colby ◽  
D I Stirling ◽  
H Dalton

1. Methane mono-oxygenase of Methylococcus capsulatus (Bath) catalyses the oxidation of various substituted methane derivatives including methanol. 2. It is a very non-specific oxygenase and, in some of its catalytic properties, apparently resembles the analogous enzyme from Methylomonas methanica but differs from those found in Methylosinus trichosporium and Methylomonas albus. 3. CO is oxidized to CO2. 4. C1-C8 n-alkanes are hydroxylated, yielding mixtures of the corresponding 1- and 2-alcohols; no 3- or 4-alcohols are formed. 5. Terminal alkenes yield the corresponding 1,2-epoxides. cis- or trans-but-2-ene are each oxidized to a mixture of 2,3-epoxybutane and but-2-en-1-ol with retention of the cis or trans configuration in both products; 2-butanone is also formed from cis-but-2-ene only. 6. Dimethyl ether is oxidized. Diethyl ether undergoes sub-terminal oxidation, yielding ethanol and ethanal in equimolar amounts. 7. Methane mono-oxygenase also hydroxylates cyclic alkanes and aromatic compounds. However, styrene yields only styrene epoxide and pyridine yields only pyridine N-oxide. 8. Of those compounds tested, only NADPH can replace NADH as electron donor.


INEOS OPEN ◽  
2021 ◽  
Vol 4 ◽  
Author(s):  
M. A. Arsenov ◽  
◽  
D. A. Loginov ◽  

The discovery of transition metal-catalyzed selective activation of aromatic carbon–hydrogen bonds in 1993 has opened a new era in the synthesis of carbo- and heterocyclic compounds. This review covers the applications of oxidative annulations of aromatic compounds with alkynes involving CH activation for the synthesis of isocoumarins and polyaromatic hydrocarbons (PAHs). The limitations, advantages, and mechanical aspects of this approach as well as the current tendencies in the application of the reaction products for photoactive materials are discussed.


1958 ◽  
Vol 36 (6) ◽  
pp. 949-951 ◽  
Author(s):  
Owen H. Wheeler

Polycyclic aromatic compounds can, in a number of cases, be oxidized with chromyl chloride, whereas heterocyclic compounds are unaffected.


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