Carbon atoms deoxygenation

In a study of the deoxygenation of carbonyl compounds by atomic carbon, Dewar and coworkers (8UA2802) presented experimental and theoretical evidence that the carbonyl group can react with carbon atoms to form a carbenaoxirane. 

Reaction of Carbon Atoms with Alcohols and Ethers. The electro-philicity of atomic carbon and the exothermicity of carbon monoxide formation in its reactions facilitates attack on, and removal of oxygen by C atoms. Deoxygenation of ethers, alcohols, and carbonyl compounds has been reported. This process is generally a highly exothermic reaction, which is likely to generate products with excess energy. 

Cyclobutanone has been deoxygenated to give carbon monoxide and cyclobutylidene by reaction with atomic carbon atoms generated from the pyrolysis of 5-tetrazolyldiazonium chloride (31). As expected, cyclobutylidene (2) rearranges under these conditions to afford, in a total yield of only 3.8 %, a mixture of methylenecyclopropane (3), cyclobutene (32) and buta-l,3-di-ene (33) in a ratio of 66 10 24.12... 

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