By Geoffrey Wilkinson
V. 1. concept & historical past -- v. 2. Ligands -- v. three. major crew & early transition parts -- v. four. heart transition parts -- v. five. past due transition parts -- v. 6. functions -- v. 7. Indexes
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Extra info for Comprehensive coordination chemistry: the synthesis, reactions, properties & applications of coordination compounds
When electrophilic substitutions of simple pyridines are successful, they require very vigorous conditions and proceed only at C-3, which is the least deactivated position. A miniscule yield of 3-nitropyridine using the standard nitrating mixture applied at an outrageously high temperature, and the vigorous conditions necessary to produce 3-bromopyridine illustrate this well (a practical conversion of pyridines into 3-nitropyridines is described on page 37). g. AlCl3), which totally resist electrophilic C-substitution.
14. 2,3-Dihydrofuran reacts with acrolein to give an adduct C7H10O2; reaction of this with aq. H2NOH–HCl gives a pyridine, C7H9NO; what is its structure? 6 Diazines The diazines – pyridazine, pyrimidine and pyrazine – show many similarities to pyridines with respect to their reactivities, but to an exaggerated degree. In particular, the presence of two nitrogens, both as imines, results in increased electron deﬁciency at carbon and hence an increased susceptibility to nucleophilic addition but an increased resistance to electrophilic attack.
Imines and enamines are often intermediates, whether stable or not, en route, via a series of equilibria, to an aromatic heterocycle. Common Reaction Types in Heterocyclic Chemistry 19 Common synthetic equivalents of carbonyl compounds in ring synthesis Quite frequently, and especially in heterocyclic ring synthesis, a reaction component is replaced with a molecule that reacts in the same way – serves the same purpose – as the traditional or classical component. For example, a ring synthesis might require a 1,3-diketone – a 3-alkoxy-enone would serve instead; a conjugated yne-one is also equivalent to a 1,3-diketone and so is a 3-dialkylamino-enone.
Comprehensive coordination chemistry: the synthesis, reactions, properties & applications of coordination compounds by Geoffrey Wilkinson