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Synthetic and Mechanistic Organic Chemistry by Boschke F.L.

By Boschke F.L.

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C, 1747 (1971). 49) Beckwith, A. L. , Leydon, R. : Austral. J. Chem. 21, 817 (1968). : Gazz. Claim. Ital. 104, 471 (1974). : Tetrahedron Lett. 4405 (1968). 5~) Timnrtlake, J . , Hodges, M. : Tetrahedron Lett. 1970, 4147. , Gardini, G. , Perchinunno, M. : Tetrahedron Lett. 27, 3655 (1971). , Russel, P. , Sutchiffe, L. : Chem. Commun. 970 (1971). 55) Kochi, J. : Free radicals (ed. J. K. Kochi), Vol. II, p. 670. New York: Wiley and Sons 1973. 56) Gardini, G. : Tetrahedron Lett. 1972, 4113. , Gardini, G.

This dramatic difference of behavior has been interpreted in terms of transition state 61). The benzene series has not enough electron-deficient character to determine a transition state similar to a charge-transfer complex, so that the reaction rates would be affected more by the stability of the intermediate cyclohexadienyl radicals (23, 24) than by polar effects + R~~ C=-N* 23 OCHa *O--CH3 24 In protonated pyridine series, a transition state similar to a charge-transfer complex (21) would allow the clear distinguishing even of carbon free radicals differing little in nucleophilicity, such as methyl, cyclopropyl and phenyl radicals.

71) Benson, S. : J. Chem. Ed. 42, 502 (1965). 72) Jones, S. : Intl. J. Chem. Kinetics, 2, 479 (1970). 7s) Zavitsas, A. , Pinto, J. : J. Amer. Chem. Soc. 94, 7390 (1972). 74) Solly, R. , Benson, S. : J. Amer. Chem. Soe. 93, 1592 (1971). 75) Alfossi, Z. , Golden, D. : J. Amer. Chem. Soc. 95, 319 (1973). 76) Dixon, W. , Norman, R. O. : J. Chem. Soc. 1964, 4857. 77) Krusic, P. , I~ettig, T. A. : J. Amer. Chem. Soc. 92, 722 (1970). : J. C. s. Perkin II, 1477 (1972). 79) Fessenden, R. , Schuler, R. : J.

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