مشخصات پژوهش

عنوان	Synthesis and Dynamic NMR study of some N-vynilated derivatives of N- phenylformamide
نوع پژوهش	مقاله ارائه شده کنفرانسی
کلیدواژه‌ها	N- phenylformamide, Acetylenic esters, Dynamic NMR Study
چکیده	There are many studies on the reactions between NH-acids and acetylenic esters in the presence of various nucleophils [1-2]. In most cases, the reactions was viewed as starting from the initial formation of zwitterionic intermediate derived from the addition of nucleophili to activated alkyne. Azide anion usually react as a nucleophil in nucleophilic substitution reactions [3] and on the basis of our knowledge, there is no any reporte about catalytic behavior of azide anion in the above reactions. Herein we report that reaction of N-phenylformamid with acetylenic esters such as alkyl propiolates or dialkyl acetylenedicarboxylates in the presence of a catalytic amount of sodium azide in dichloromethane leads to alkyl 3-(formylanilino)-2-propenoates and dialkyl 2-(formylanilino)-2-butenedioates in good yields. Dynamic NMR effects are observed in the 1H NMR spectra of the title compounds as a result of restricted rotation around the N-formyl bond. The free energy of activation (∆G≠) for this process is 64-66 ± 2 KJmol-1.
پژوهشگران	مهدی اسدیان (نفر دوم)، فاروق نصیری (نفر اول)