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Phosphonium Phenolate Zwitterion vs Phosphonium Ylide: Synthesis, Characterization and Reactivity Study of a Trimethylphosphonium Phenolate Zwitterion
Author(s) -
Xiao Jing,
Li Qiang,
Shen Ruwei,
Shimada Shigeru,
Han LiBiao
Publication year - 2019
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201901303
Subject(s) - zwitterion , phosphonium , chemistry , ylide , reactivity (psychology) , medicinal chemistry , tautomer , organic chemistry , molecule , medicine , alternative medicine , pathology
4‐Methoxy‐3‐(trimethylphosphonio)phenolate was obtained from a regioselective addition of PMe 3 to p ‐quinone monoacetal. This compound undergoes hydrogen isotope exchange with D 2 O or CD 3 CN, and is capable of catalyzing H/D exchange of CD 3 CN with substrates bearing weakly acidic hydrogens. It exhibits similar reactivity to phosphorus ylides for olefinations of aldehydes. A possible tautomerization between the phosphonium phenolate zwitterion and phosphonium ylide is proposed for the first time to rationalize the unique reactivity.