کد مقاله کد نشریه سال انتشار مقاله انگلیسی نسخه تمام متن
1325126 977369 2011 5 صفحه PDF دانلود رایگان
عنوان انگلیسی مقاله ISI
N-(ethoxycarbonyl)ferrocenecarboxamide: Synthesis and use as the pronucleophile in the Mitsunobu reaction
موضوعات مرتبط
مهندسی و علوم پایه شیمی شیمی معدنی
پیش نمایش صفحه اول مقاله
N-(ethoxycarbonyl)ferrocenecarboxamide: Synthesis and use as the pronucleophile in the Mitsunobu reaction
چکیده انگلیسی

The title compound has been synthesized in the reaction of ferrocene with ethoxycarbonyl isocyanate in methanesulfonic acid. It has been found that it undergoes N-alkylation with benzyl alcohols under classical Mitsunobu conditions (PPh3/DEAD). However, in the reaction with cholesterol and stigmasterol O-alkylation with inversion of configuration occurred (confirmed by hydrolysis of the product obtained from cholesterol to epicholesterol). The structure of the product obtained from p-nitrobenzyl alcohol was determined by X-ray diffraction.

N(ethoxycarbonyl)ferrocenecarboxamide reacts with alcohols under classical Mitsunobu conditions (PPh3/DEAD) to afford, depending on the structure of alcohol, products of N- or O-alkylation.Figure optionsDownload as PowerPoint slideHighlights
► The submitted paper describes a one-step synthesis of a ferrocenyl amide having an ester subtituent at the nitrogen atom.
► This compound undergoes Mitsunobu reactions with alcohols to afford products of N- or O-alkylation.
► The reaction opens a novel synthetic entry to a variety of ferrocene derivatives.
► It has been used for synthesis of ferrocenyl derivatives of cholesterol and stigmasterol.

ناشر
Database: Elsevier - ScienceDirect (ساینس دایرکت)
Journal: Journal of Organometallic Chemistry - Volume 696, Issue 23, 15 November 2011, Pages 3826–3830
نویسندگان
, , ,