Organometallic compounds with peroxides

Lawesson Yang J. Am. them. Soc. 1959,81, 4230 Lawesson Frisell Denney, Denney Tetrahedron 1963, 19, 1229. For a monograph on the reactions of organometallic compounds with peroxides, see Ref. 298. For a review, see Razuvaev Shushunov Dodonov Brilkina, in Swern Organic Peroxides, vol. 3 Wiley New York. 1972, pp. 141-270. 

T. G. Brihnka and V. A. Shushunov, Reactions of Organometallic Compounds with Ouygen and Peroxide, CRC Press, Inc., Cleveland, Ohio, 1969, pp. 184-185. 

For a monograph, sec Brilkina Shushunov Reactions of Organometallic Compounds with Oxygen and Peroxides, CRC Press Boca Raton, FL, 1969. For a review, sec Wardcll Paterson, in Hartley Palai, Ref. I. vol. 2, 1985 pp. 219-338. pp. 311-316. 

Brilkina T.G, Shushunov V.A, Reactions of Organometallic Compounds with Oxygen and Peroxides, Nauka, Moscow, 1966... 

Berlin, L.E. (Tr. Nauch. Inst. Moscow 1958 49, cited in Brilkina, T.G. Shushunov, V.A., Reactions of Organometallic Compounds with Oxygen and Peroxides, Iliffe, London 1969, p. 158). 

Razuvaev, G.A. Shushunov, V.A. Oodonov, V.A. Brilkina, T.G. (in Swern, D., Organic Peroxides, Vol. 3, Reactions of Organometallic Compounds with Organic Peroxides, WIley-Interscience, New York 1972, pp. 141/270). 

Not only alkenes and arenes but also other types of electron-rich compound can be oxidized by oxygen. Most organometallic reagents react with air, whereby either alkanes are formed by dimerization of the metal-bound alkyl groups (cuprates often react this way [80]) or peroxides or alcohols are formed [81, 82]. The alcohols result from disproportionation or reduction of the peroxides. Similarly, enolates, metalated nitriles, phenolates, enamines, and related compounds with nucleophilic carbon can react with oxygen by intermediate formation of carbon-centered radicals to yield dimers (Section 5.4.6 [83, 84]), peroxides, or alcohols. The oxidation of many organic compounds by air will, therefore, often proceed faster in the presence of bases (Scheme 3.21). 

Acyl and alkyl peroxides and hydroperoxides. with organometallic compounds... 

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