Handbook of Heterocyclic Chemistry by Alan R. Katritzky (Auth.)

By Alan R. Katritzky (Auth.)

This new version is designed to supply a one-volume total photograph of the topic of heterocyclic chemistry

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Extensive randomization of ring hydrogen atoms, which increases with increasing lifetime of the ions, takes place prior to fragmentation, as does independent scrambling of ring carbon atoms. iii) are also common. The mass spectra of the aromatic six-membered heterocycles and their benzo analogues reflect the stability of the ring systems, with the molecular ion in many cases also being the base peak. Fragmentation of the azines by loss of HCN (Af-27) is the common pathway and for pyridine the M-27 ion is the only fragment of any significance in the spectrum apart from the molecular ion.

9 0 ^ 9 1 ) , and their migration from one position to another is sometimes rapid enough for the system to be considered tautomeric. 4 Ring-Chain and Valence Bond Tautomerism Ring-chain tautomerism can occur when a substituent group can interact with an NH group or nitrogen atom of a heterocyclic ring. An example of the first case is provided by the 1,2,4-triazinone side-chain aldehydes (92a) and (92b) which exist in equilibrium with the cyclized forms. The second possibility is illustrated by a-azidoazines which exist in equilibrium with tetrazolefused systems: thus, 2-azido-l,2,4-triazines (93a) exist predominantly as the tetrazolotriazines (93b).

Maleic anhydride is frequently used as a dienophile in Diels-Alder reactions and it is a component of alkyd resins. Several unsaturated y-lactones are natural products, while the furanose sugars are cyclic hemi-acetals. Thiophene and its homologues occur in coal-tar benzene, shale oil and crude petroleum. ii), and the discovery of thiophene followed the observation that pure benzene did not give this test. g. thiotolene for methylthiophene, thiotenol for hydroxythiophene. 15). Pyrrole occurs in bone oil and imparts a bright red color to pine wood moistened with mineral acid; this characteristic behavior led to its discovery and is used as a qualitative test for pyrrole derivatives.

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