Azulenes formation

Azulene formation from indanes and diazoacetates. Cf. Buchner ring expansion. 

Shemdal considers the formation of a crystalline picrate, melting at 122°, the best method of identifying azulene. On reduction azulene yields a dihydro-sesquiterpene, and in Sherndal s opinion, it is... 

Polycyclic aromatic hydrocarbons, indole and quinoline derivatives, naphthylamines, azulenes Silica gel G Formation of oxidation products via the initially formed iodine complexes [15]... 

The predicted conrotatory cyclization of octatetraenes was confirmed for the case of the methyl-substituted compounds, which above 16 °C readily formed the cyclooctatrienes shown in equations 13 and 14)14. We conclude this section with an electrocyclic reaction involving ten TT-electrons, that is, the formation of azulene (17) when the fulvene 16 is heated (equation 15)15,16. 

Table I summarizes the pKR+ values and redox potentials for the tri(l-azulenyl)methyl cations. The oxidation exhibited a barely separate two-step, two-electron oxidation wave. This wave is ascribed to the oxidation of two azulene rings to generate a tricationic species. The reduction showed a one-electron wave, which is ascribed to the formation of a neutral radical.

The interpretation of these effects as the formation of a proton addition complex was further supported by Plattner et al. (1952) by means of spectroscopic and conductimetric investigations. In these interactions the change of the absorption spectrum is characteristic, since the blue colour of the azulene in organic solvents is changed to a yellow colour in... 

Of particular interest is the observation that in certain cases products such as 24 resulting from domino processes are obtained After the formation of the furan, evidently a double Michael-type addition of these intermediates to the remaining starting material 23 can take place at the unsubstituted 5-position. Preliminary experiments to investigate scope and limitations of such addition reactions in the presence of gold salts also confirm the applicability to the functionalization of other electron-rich arenes (Scheme 6) Besides furans, azulene 28 and di- and trialkoxybenzene are suitable as nucleophiles for the reaction with unsaturated carbonyl compounds [14]. For instance, 2-methylfuran (25) reacts at the reactive 5-position with methyl vinyl ketone 26 to give the addition product 27, and with azulene 28 a twofold... 

Azeotropic distillation, 20,66,106,23,38 Azide, formation from a hydrazine, 22,96 Azobenzene, 22, 28 Azoyl chloride, 25, 87 Azulene, removal from a hydrocarbon, 24, 86... 

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