Cascade reaction of propargylic alcohols with hydroxylamine hydrochloride: facile synthesis of α, β-unsaturated oximes and nitriles. Issue 44 (3rd November 2016)

• Record Type: Journal Article
• Authors: Zhang, Qi; Zhang, Linjing; Tang, Chaojun; Luo, Huan; Cai, Xuediao; Chai, Yonghai
• Is Part Of: Tetrahedron. Volume 72:Issue 44(2016)
• Page Start: 6935
• Page End: 6942
• Publication Date: 2016-11-03
• Subjects: α, β-unsaturated oximes -- α, β-unsaturated nitriles -- Propargylic alcohols -- Hydroxylamine hydrochloride -- Organic acid -- Dehydrating promoter; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tet.2016.09.010
• Languages: English
• ISSNs: 0040-4020

Abstract

Abstract: We have developed an easy and practical method for the synthesis of α, β-unsaturated oximes and nitriles from readily available propargylic alcohols with hydroxylamine hydrochloride (NH2 OH·HCl) under metal-free conditions. By using or not using p -toluenesulfonyl chloride ( p -TsCl) as the dehydrating promoter, the desired nitriles or oximes could be obtained, respectively via a three-step one-pot or two-step one-pot process in moderate to excellent yields with good functional group compatibility. Graphical abstract: