The bromination of N,N-disubstituted anilines was performed in aqueous suspension of 1-hexadecylpyridinium tribromide (CPyBr3), using the surfactant counterion as reagent. The experiments carried out at room temperature showed the same regioselectivity observed in homogeneous solutions, with the prevalence of the para-bromo product. On the contrary, at 0 ◦C the [ortho-bromo]/[para-bromo] ratio increased. This result can be ascribed to the location of the aniline at the solid–water interphase and to the tight packing at low temperature.
Surfactant control of the ortho/para ratio in the bromination of anilines. 4
CERICHELLI, GIORGIO;
2006-01-01
Abstract
The bromination of N,N-disubstituted anilines was performed in aqueous suspension of 1-hexadecylpyridinium tribromide (CPyBr3), using the surfactant counterion as reagent. The experiments carried out at room temperature showed the same regioselectivity observed in homogeneous solutions, with the prevalence of the para-bromo product. On the contrary, at 0 ◦C the [ortho-bromo]/[para-bromo] ratio increased. This result can be ascribed to the location of the aniline at the solid–water interphase and to the tight packing at low temperature.File in questo prodotto:
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