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Alan R. Katritzky (ed.)'s Advances in Heterocyclic Chemistry, Vol. 34 PDF

By Alan R. Katritzky (ed.)

ISBN-10: 012020634X

ISBN-13: 9780120206346

Meant for natural chemists, this quantity follows the layout of past volumes and gives updated info on chosen components of heterocyclic chemistry.

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67 . . . . 68 68 68 68 . . . . . . . . . . . . Copyrighl @ 1983 by Academic Press. Inc . All rights of reproduction in any form reserved. ISBN-0- 12-020634-X 54 MICHAEL P. SAMMES AND ALAN R. KATRITZKY 1. Migration of 4-Substituent . . . . . 2. Cope Rearrangements . . . . . . 3. Rearrangements of Salts . . . . . . Photochemical Reactions Formally Involving No Other Species ReactionsofRingAtomswithElectrophiles . . . 1. Salt Formation . . . . . . . 2. Complex Formation .

Jaxa-Chamiec, W. S. McDonald, P. G . Sammes, and R. R . Talekar, Tetrahedron Left. 23,2813 (1982). 17' J. M. Bolster and R . M. Kellogg, J. Org. Chem. 47, 4429 (1982). 176 D. G. Heath and C. W. Chem. , 1280 (1982). 177 A. D. C. Caruso, and A. Padwa, Tetrahedron Lett. 23, 2167 (1982). 174 ADVANCES IN HETEROCYCLIC CHEMISTRY. VOL . 34 The 4H-Pyrazoles MICHAEL P. SAMMES Department of Chemistry. University of Hong Kong. Hong Kong ALAN R . KATRITZKY Department of Chemistry. University of Florida. Gainesville.

Ll7 c . Aryl, Benzyl, or Alkyl Group at C-3. When C-4 is unsubstituted, alkyl and aryl groups have migrated exclusively to this atom, giving 1Hpyrazoles ~ 3 ~ ~ l 0 - l 2 . l 5 , 1 8 , l 9 , 4 3 . 4 6 . 5 3 . "' Aryl groups migrate to the exclusion of alkyl g r o ~ p s , ' ~ ' ~ . ' ' ' which ~ " ~ ~ them'~~ selves move only at high t e m p e r a t u r e ~ . DMSO FNMe MecN Me + H (145) (146) (147) SCHEME 47 For the cases where all carbon atoms are fully substituted, competitive migration occurs to C and N, giving 129 (or its degradation products) and 131.

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Advances in Heterocyclic Chemistry, Vol. 34 by Alan R. Katritzky (ed.)


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