| Abstract
| - 4-Alkyl-2-nitrothiophenes [10: R = CH3, CH(OH)CH3, CH(OCH3)CH3] react with secondary aliphaticamines, in the presence of AgNO3, to give 3-alkyl-2-amino-5-nitrothiophenes (12) through an oxidativenucleophilic substitution of hydrogen (ONSH) of synthetic interest. This behavior is in striking contrastwith that of the parent 2-nitrothiophene (6), which was found to undergo ring-opening in analogousreaction conditions. A possible rationale for the crucial effect of alkyl groups is suggested, groundedalso on a study of the corresponding Meisenheimer-like adducts.
|
