Advances in Heterocyclic Chemistry, Vol. 27 by A.J.Boulton A.R. Katritzky

By A.J.Boulton A.R. Katritzky

(from preface)Volume 27 includes 4 contributions. Black and Doyle speak about '' l-Azabicyclo[3.1.0]hexanes and Analogs with extra Heteroatom Substitution.'' half II of the therapy of ''Heteroaromatic Radicals'' by way of Hanson offers with radicals with workforce VI heteroatoms and completes the overview of the heteroaromatic unfastened radicals began in quantity 25. In ''The 1,2- and 1,3-Dithiolium Ions.'' Lozac'h and Stavaux increase thus far the overview by means of Prinzbach and Futterer which seemed in 1966 in quantity 7 of this e-book. ultimately, Grimmett has up to date his personal evaluate of im-idazole chemistry which seemed in 1970 in quantity 12.

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Tetramethyl-p-phenylenediamine (TMPD) transfers one electron l~~ and ESR spectroscopy shows 29 and TMPD" to r e ~ u 1 t . A l ~comparison ~ suggested an outer-sphere activated complex. A scale of the relative stabilities of the various radicals was deduced. Since 29 results when 2,4,6-triphenylC. Gaze, B. C. Gilbert, and M. C. R. Symons, J . C. S . Perkin ZZ 235 (1978). E. A. C. Lucken and B. Poncioni, J . C. S. Perkin IZ, 777 (1976). 13' S. Hunig, G. Kiesslich, F. Linhart, and H. Schlaf, Justus Liebigs Ann.

Marcoux, and A. J. Bard, J. Am. Chem. 94, 5538 (1972). 49 H. Kojima and A. J. Bard, J. Am. Chem. Soc. 97,6317 (1975). 5 0 F. Gerson, W. Huber, and 0. Wennerstrom, Hrlu. Chim. Acta 61, 2763 (1978). 5 ’ Ya. P. Stradins. S. A . Hillers, R. A. Gavars, G . 0. Reihmanis, and L. Kh. Baumane, Experientia, Suppl. 18, 607 (1971). 5 2 R. A . Gavars. Ya. P. Stradins, and S. A. Hillers, Dokl. Akad. Nauk SSSR 157, 1424 (1964) [ C A 62, 3667 (1965)l. 44 45 38 [Sec. ^^-'^ The work has involved calculation of the spin distribution in 5-substituted 2-nitrofuran a n i o n - r a d i ~ a l s ~as~ ,well ~ as an investigation of the manner in which the spin distribution varies markedly with solvent, co-solutes, etc.

Chem. 72, 3641 (1968). 174 K. Maruyama, M. Yoshida, and K. Murakami, Bull. Chem. Jpn. 43, 152 (1970). 175 L. Lunazzi, A. Mangini, G . Placucci, and C. Vincenzi, J . C. S. Perkin I , 2418 (1972). 1 7 6 M. Hori, T. Kataoka, Y. Asachi, and E . Mizuta, Chem. Phurm. Bull. 21, 1318 (1973). Y. Yamada, S. Toyoda, and K . Ouchi, J. Phys. Chem. 78,2512 (1974). 16' 16* '" Sec. 07 (39) 0 853 of other authors, preferred 63"174; Lunazzi et al. suggested 70-80",175 while Yamada et required only 54". Moreover, the last workers detected significant differences in the heterocyclic proton splittings between 41 on the one hand and the o-tolyl analog on the other which they ascribed to less effective delocalization through the C9-aryl bond for the more hindered radical.

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