کد مقاله | کد نشریه | سال انتشار | مقاله انگلیسی | نسخه تمام متن |
---|---|---|---|---|
1325126 | 977369 | 2011 | 5 صفحه PDF | دانلود رایگان |

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.
Journal: Journal of Organometallic Chemistry - Volume 696, Issue 23, 15 November 2011, Pages 3826–3830