Dimethyl Sulfoxide Mediated Elimination Reactions in 3-Aryl 2,3-Dihalopropanoates: Scope and Mechanistic Insights

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• 作者：Wei Li ; Jianchang Li ; Melissa Lin ; Sumrit Wacharasindhu ; Keiko Tabei ; Tarek S. Mansour
• 刊名：Journal of Organic Chemistry
• 出版年：2007
• 出版时间：August 3, 2007
• 年：2007
• 卷：72
• 期：16
• 页码：6016 - 6021
• 全文大小：173K
• 年卷期：v.72,no.16(August 3, 2007)
• ISSN：1520-6904

文摘

Dimethyl sulfoxide (DMSO) efficiently causes the reductive elimination of 3-aryl 2,3-dibromopropanoatesto cinnamates with good yield. With 3-phenyl 2,3-dihalopropanoates, debromination is the major pathwayproviding 3-phenylacrylate derivatives in high yields, whereas dehydrobromination is a competing pathwaywith thiophene derivatives. ¹H NMR, ⁸¹Br NMR, and MS techniques indicated the formation of brominated-DMSO, MeBr, and HBr as byproducts in this transformation with no evidence for the formation of Br₂.The dual role of DMSO as a nucleophile and bromine scavenger accounts for the products formed in thisreaction.