The conversion of ether bonds to hydroxyl via a base-promoted rearrangement of cyclic phosphine oxides. Issue 20 (17th August 2021)

• Record Type: Journal Article
• Authors: Li, Zhan-Cai; Zhang, Yu; Yan, Bing-Xia; Wang, Xiao-Ning; Zhai, De-Hua; Li, Qiang; Zheng, Hong-Xing; Zhao, Chang-Qiu
• Is Part Of: Organic chemistry frontiers. Volume 8:Issue 20(2021)
• Page Start: 5693
• Page End: 5698
• Publication Date: 2021-08-17
• Subjects: Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1039/d1qo00925g
• Languages: English
• ISSNs: 2052-4110

Abstract

Abstract : Biphenyl derived secondary phosphine oxides having 2′-hydroxyl were prepared. Abstract : Biphenyl derived secondary phosphine oxides having 2′-hydroxyl were prepared. The compounds were converted to hydroxymethyl phosphine oxides when reacted with formaldehyde. After chlorination and cyclization, a series of P, O-heterocycles were obtained. When treated with LDA, a rearrangement occurred to stereoselectively afford hydroxyl substituted cyclic phosphines. The rearrangement was proposed to occur via intra-molecular aromatic substitution (SN Ar) reactions, with an attack of a carbon anion on alkoxyl on an adjacent benzene cycle. P -Stereogenic secondary phosphine oxide was stereospecifically converted to a P, C, axial -stereogenic P-cycle.