Aryliminodimagnesium Reagents. XV. Condensation with Nitrobenzene. Formation of Unsymmetrical Azobenzenes Favored By Long-Chain p-Alkoxy-Substituted Reagents

Article abstract of DOI:10.1246/bcsj.62.915

In the reaction of p-MeC6H4N(MgBr)2 with p-alkoxynitrobenzene, no effect of alkoxy chain length on the relative yields of azoxy and azo products was observed.In contrast, in the reaction of p-alkoxy-C6H4N(MgBr)2 with p-nitrotoluene, C12- and C18-alkoxyl chains led to the corresponding unsymmetrical azobenzenes in unexpectedly high yields.This result, arising from efficient condensation and deoxygenation processes, was explained in terms of cooperation of reagent molecules through their aggregation assisted by a novel tying effect of their long chains.