Synthesis 2007(12): 1768-1778  
DOI: 10.1055/s-2007-983705
PAPER
© Georg Thieme Verlag Stuttgart · New York

Synthesis of Difluoromethylene-Containing 1,2,4-Oxadiazole Compounds via the Reaction of 5-(Difluoroiodomethyl)-3-phenyl-1,2,4-oxadiazole with Unsaturated Compounds Initiated by Sodium Dithionite

Xueyan Yanga, Zhonghua Wanga, Xiang Fanga, Xianjin Yanga, Fanhong Wu*a,b, Yongjia Shena
a Laboratory for Advanced Materials and Institute of Fine Chemicals, East China University of Science and Technology, 130 Meilong Rd, Shanghai 200237, P. R. of China
b Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Rd, Shanghai 200032, P. R. of China
Fax: +86(21)64253074; e-Mail: wfh@ecust.edu.cn;
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Publikationsverlauf

Received 28 February 2007
Publikationsdatum:
08. Juni 2007 (online)

Abstract

5-(Difluoroiodomethyl)-3-phenyl-1,2,4-oxadiazole, syn­thesized by the iodination of the corresponding zinc reagent of 5-(bromodifluoromethyl)-3-phenyl-1,2,4-oxadiazole, reacted with various unsaturated compounds, such as alkenes, alkynes, pent-4-en-1-ols, and pent-4-enoic acids, in the presence of sodium dithionite and sodium hydrogen carbonate in aqueous acetonitrile solution at ambient temperature to afford various difluoromethylenated 1,2,4-oxadiazole-containing compounds, including γ-butyrolactones and tetrahydrofurans, in moderate yields.