亞硝鎓離子與苯乙酮合成2-氧代-2-苯基乙烷-1,1-二基二乙酸酯之反應研究

Please use this identifier to cite or link to this item: https://ir.lib.ncu.edu.tw/handle/987654321/99225

Title:	亞硝鎓離子與苯乙酮合成2-氧代-2-苯基乙烷-1,1-二基二乙酸酯之反應研究
Authors:	李俊頡;Li, Jyun-Jie
Contributors:	化學學系
Keywords:	亞硝鎓離子;2-氧代-2-苯基乙烷-1，1-二基二乙酸酯
Date:	2026-01-27
Issue Date:	2026-03-06 18:22:39 (UTC+8)
Publisher:	國立中央大學
Abstract:	本篇論文為苯乙酮 (acetophenone) 與四氟硼酸亞硝鎓 (nitrosonium tetrafluoroborate, NOBF4) 在酸性條件下於苯乙酮的α位置進行氧化生成2-氧代-2-苯基乙烷-1,1-二基二乙酸酯 (2-oxo-2-phenylethane-1,1-diyl diacetate)，以下簡稱α-酮二乙酸酯 (a-keto diacetate)。反應機制之研究顯示：在酸性條件下，亞硝鎓離子(nitrosonium ion, NO¬+)，與苯乙酮的烯醇互變異構體 (acetophenone enol) 會生成異腈羥胺基苯乙酮 (isonitrosoacetophenone) 後，與醋酸或水進行水解取代反應，得到α-酮二乙酸酯。此方法條件溫和且反應試劑容易取得，我們利用此方法製備出 23種2-氧代-2-苯基乙烷-1,1-二基二乙酸酯衍生物，最高產率可達 91 %，期望此方法未來可以廣泛地應用於製備這類型的化合物。 ;In this study, we report the oxidation of α-position of acetophenones with nitrosonium tetrafluoroborate (NOBF4) under acidic conditions (trifluoroacetic acid/acetic acid) to afford 2-oxo-2-phenylethane-1,1-diyl diacetates. After our mechanistic study, the reaction mechanism was proposed: under the acidic condition, nitrosonium ion (NO+) reacts with the enol tautomer of acetophenone to generate isonitrosoacetophenone as the reaction intermediate. Isonitrosoacetophenone subsequently undergoes an acetic acid or water–mediated hydrolysis-like transformation to yield the α-keto diacetate. This method features mild reaction conditions and employs readily available reagents. We successfully synthesized 23 α-keto diacetates with yields of up to 91 %. We anticipate that this method will find broad application in the field of this α-keto diacetate synthesis chemistry
Appears in Collections:	[Graduate Institute of Chemistry] Electronic Thesis & Dissertation

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