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

By Alan R. Katritzky (ed.)

ISBN-10: 012020634X

ISBN-13: 9780120206346

Meant for natural chemists, this quantity follows the structure of earlier volumes and gives up to date details on chosen parts of heterocyclic chemistry.

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68 69 70 71 72 72 72 72 73 73 13 74 74 76 76 78 1. Introduction As was pointed out in the preceding chapter,’ pyrazoles are known in two nonaromatic forms (the 3H- and 4H-pyrazoles, Scheme 1) in addition to the more familiar aromatic 1H form. The 3H-pyrazoles, which may be considered as cyclic vinylazo compounds, have been discussed in reference 1; the 4H-pyrazoles, which are cyclic azines, are the subject of this review.

OAc 46 [Sec. B MICHAEL P. SAMMES AND ALAN R. KATRITZKY 2. Rearrangements with Retention of Nitrogen a. Valence Isomerization. O]pent~ ' ~reac~~~@ 2-enes (166) via a 4 7 ~disrotatory electrocyclic ring c I o s ~ r e . ' ~ The tion has been observed only for fully alkyl-substituted pyrazoles; systems having R' and/or R2 # alkyl give only cyclopropenes 167. It is remarkably solvent-dependent, giving exclusively 166 in methanol and dichloromethane, but increasing amounts of 167 also, as solvent polarity d e c r e a ~ e s .

Structure . . . . . . . . 1 . Tautomerism . . . . . . 2 . Dipole Moments . . . . . . B . Spectroscopic Properties . . . . . 1 . Ultraviolet Spectra . . . . . . 2 . Infrared Spectra . . . . . . 3 . 'H-NMR Spectra . . . . . . 4 . I3C-NMR Spectra . . . . . . 5 . Mass Spectra . . . . . . . 6. Photoelectron Spectra . . . . . IV . Chemical Reactions . . . . . . . A . Thermal Reactions Formally Involving No Other Species 53 . . . . . .

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


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