By Alan R. Katritzky (ed.)
Meant for natural chemists, this quantity follows the structure of earlier volumes and offers updated info on chosen components of heterocyclic chemistry.
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54 . 55 . 55 . 56 . 56 . 57 . 58 . 58 . 59 . 59 . 60 . 61 . 62 . 62 . 64 . 64 . 65 . 65 . 65 . 65 . 65 . 65 . 66 . 67 . . . . 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 .
Freeman, E. R . Janiga, and J . F. Lorenc. J. Org. Chem. 42, 3721 (1977). J . P. Freeman and E. R . Janiga, J. Org. Chem. 39, 2663 (1974). W. R . Dolbier, Jr. and W. M. S. Chem. , 289 (1970). R . Paredes and W. R . , Rev. Latinoam. Quim. 6, 29 (1975) [CA 83, 8773p ( 1975)). 26 [Sec. H MICHAEL P. SAMMES AND ALAN R. KATRITZKY 2. Il8 Hypobromite oxidation of 97 leads to the same compound’29(Scheme 3 9 , whereas the 4-bromo analog of 96 has been prepared by base elimination of HBr from a dibromopyrazoline N,N’-dioxide p r e c u r ~ o r .
The formation of 117 from 116 (Scheme 40). 2. de process, though more favorable in terms of heat of reaction than cycloreversion to diazomethane S. Mataka and M. Tashiro, J. Org. Chem. 46, 1929 (1981). Sec. A] 39 THE 3H-PYRAZOLES p2-!? R‘=H \ \ / g / H SCHEME 49 + P N C 0 C0,Me , M e + ( 155) SCHEME 50 and ethyne, or three-piece fragmentation to triplet methylene, nitrogen, and ethyne. '^^^^ It appears to occur most readily, however, when it results in release of steric constraint in the 3H-pyrazole as in 62 (Scheme 21),’04and particularly when the resulting vinyldiazo compound is stabilized by extensive conjugation.