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Intramolecular reactions of diazocarbonyl compounds
Intramolecular reactions of diazocarbonyl compounds include addition to carbon–carbon double bonds to form fused cyclopropanes and insertion into carbon–hydrogen bonds or carbon–carbon bonds.〔Burke, S. D.; Grieco, P. A. ''Org. React.'' 1979, ''26'', 361. 〕
==Introduction==
In the presence of an appropriate transition metal (typically copper or rhodium 〔Davies, H.; Antoulinakis, E. ''Org. React.'' 2001, ''57'', 1.〕), α-diazocarbonyl compounds are converted to transition metal carbenes, which undergo addition reactions in the presence of carbon–carbon double bonds to form cyclopropanes.〔Stork, G.; Ficini, J. ''J. Am. Chem. Soc.'' 1961, ''83'', 4678.〕 Insertion into carbon–carbon or carbon–hydrogen bonds is possible in substrates lacking a double bond.〔Nakata, T.; Tahara, A. ''Tetrahedron Lett.'' 1976, 1515.〕 The intramolecular version of this reaction forms fused carbocycles, although yields of reactions mediated by copper are typically moderate. For enantioselective cyclopropanations and insertions, both copper- and rhodium-based catalysts are employed, although the latter have been more heavily studied in recent years.〔Doyle, M.; Forbes, D. ''Chem. Rev.'' 1998, ''98'', 911.〕
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