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Oxidative cleavage: A reaction in which a carbon-carbon bond is cleaved, with simultaneous oxidation of the carbons that had formed the carbon-carbon bond. Alkyne ozonolysis is an oxidative cleavage reaction.
Many oxidation-reduction (redox) enzymes, particularly oxygenases, have roles in reactions that make and break C-C bonds.
Carbon-carbon single bond is very strong. C-C bond energy is 348 kJ/mol . Because of the great bond enthalpy, the bond can survive high temperatures. Hence, carbon can form large molecules by forming bond with itself.
Three specific enzymes are discussed: pyruvate-formate lyase (PFL), spore photoproduct lyase (SPL), and benzylsuccinate synthase (BSS). What these enzymes have in common is that they use radical chemistry to catalyze C?C bond formation or cleavage reactions.
In this regard, the mechanism proposed for cleaving the C?C bond comprises a series of C?H bond cleavage reactions to access a benzyne-type intermediate [h2-C2-C6H4(NCCN)]W(PMe3)4H2, from which [k2-C2-C6H4(NC)2]W(PMe3)4 is obtained via a sequence that involves reductive elimination of H2 and C?C bond cleavage.