The conversion of ether bonds to hydroxyl via a base-promoted rearrangement of cyclic phosphine oxides
Literature Information
Publication Date
2021-08-05
DOI
10.1039/D1QO00925G
Impact Factor
5.281
Authors
Zhan-Cai Li, Yu Zhang, Bing-Xia Yan, Xiao-Ning Wang, De-Hua Zhai, Qiang Li, Hong-Xing Zheng, Chang-Qiu Zhao
View Original
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 (SNAr) 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.
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Source Journal
Organic Chemistry Frontiers
CiteScore:
7.8
Self-citation Rate:
8.7%
Articles per Year:
724
Organic Chemistry Frontiers publishes high-quality research from across organic chemistry. Emphases are placed on studies that make significant contributions to the field of organic chemistry by reporting either new or significantly improved protocols or methodologies. Topics include, but are not limited to the following: Organic synthesis Development of synthetic methodologies Catalysis Natural products Functional organic materials Supramolecular and macromolecular chemistry Physical and computational organic chemistry
Recommended Compounds
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N-[(1R,2R)-2-Amino-1,2-diphenylethyl]-1,1,1-trifluoromethanesulfonamide
CAS Number:
852212-89-6
Molecular Formula:
C15H15F3N2O2S
![4-[(2-Fluoro-4-methylphenyl)amino]-6-[4-(2-hydroxyethyl)-1-piperazinyl]-7-methoxy-3-cinnolinecarboxamide structure](https://static.chemtradehub.com/structs/104/1041852-85-0-fb1c.webp "4-[(2-Fluoro-4-methylphenyl)amino]-6-[4-(2-hydroxyethyl)-1-piperazinyl]-7-methoxy-3-cinnolinecarboxamide structure")
4-[(2-Fluoro-4-methylphenyl)amino]-6-[4-(2-hydroxyethyl)-1-piperazinyl]-7-methoxy-3-cinnolinecarboxamide
CAS Number:
1041852-85-0
Molecular Formula:
C23H27FN6O3
1-(3-Bromophenyl)-4-oxocyclohexanecarboxylic acid
CAS Number:
1385694-53-0
Molecular Formula:
C13H13BrO3
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