By Alan R. Katritzky
(from preface)Volume forty seven of Advances in Heterocyciic Chemistry is, not like so much volumes, a monograph and bargains with the quantitative points of electro-philic substitution of heterocycles. it really is written by means of Roger Taylor of the college of Sussex, Brighton, England, and your editor with one bankruptcy contributed by means of Ross Grimmett of the collage of Otago in New Zealand. it really is was hoping that this survey of the entire quarter of electrophilic substitution of heterocycles, overlaying because it does semiqualitative in addition to thoroughly quantitative elements, should be of substantial support to employees within the field.As is basic for volumes of our sequence, no topic index is integrated. as a substitute, there's a very designated contents from which we think it will likely be attainable to trace down so much issues. in fact, this quantity could be listed in quantity fifty one. with a view to be the following ''index volume'' of the sequence and should conceal Volumes 46-50, simply as quantity forty six coated Volumes 41-45 and quantity forty coated Volumes 1-40.
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Additional resources for Advances in Heterocyclic Chemistry
Species variation of the following types must be considered. (1) Different charge types in rapid equilibrium. , 2,6-diaminopyridine/monocation/dication). , 6-chloro-2-pyridone/6-chloro-2hydroxypyridine). , in certain pyrimidines exchange can occur via covalently hydrated species). (4) Complications (1)-(3) can occur simultaneously. , in pyridinium cation, can occur in zwitterions o r ylids). , (1) and ( S ) ] is distinguished by examination of rate profiles. Comparison with fixed models is needed, however, to distinguish between species of the same charge type [(2) or (3)], and this method can also be used to help distinguish different charge types.
2) Rates may be measured over very wide acidity and temperature ranges. (3) Steric hindrance is absent. (4) Aqueous acids may be used in which the acidity function behavior is much better understood than for any other solvent. 28 2. HYDROGEN EXCHANGE [Sec. G ( 5 ) By choosing the appropriate acidity and temperature range, a very large range of heteroaromatic compounds of widely differing reactivity can be made to undergo acid-catalyzed exchange. The mechanism of heteroaromatic hydrogen exchange can therefore be determined for a wide variety of substrates in the manner described in the previous sections; in particular, the nature of the species undergoing reaction may be elucidated.
3) is rate-determining, so that the reaction is first-order in both nitronium ion (or its precursor) and aromatic. The last step, Eq. 4), is fast except in the case of nitration of some substituted 1,3,5-tri-t-butylbenzenes (but not the parent compound), where the exceptional steric hindrance causes the reverse step of Eq. 3) to become fast relative to the forward step of Eq. 4) (60ACS219; 66JA1569; 68JA2105). B. ENCOUNTER CONTROL A more recently recognized kinetic complication is that, for all aromatics more reactive than toluene, Eq.
Advances in Heterocyclic Chemistry by Alan R. Katritzky