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The Synthesis and Mechanistic Considerations of a Series of Ammonium Monosubstituted H ‐Phosphonate Salts
Author(s) -
Lee Keng Lung,
Feld Joey,
Hume Paul,
Söhnel Tilo,
Leitao Erin
Publication year - 2021
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.202003090
Subject(s) - phosphonate , chemistry , alkylation , substituent , amine gas treating , medicinal chemistry , alkyl , yield (engineering) , ammonium , phenol , reactivity (psychology) , solvent , organic chemistry , catalysis , medicine , materials science , alternative medicine , pathology , metallurgy
Abstract A series of ammonium monosubstituted H ‐phosphonate salts were synthesized by combining H ‐phosphonate diesters with amines in the absence of solvent at 80 °C. Variation of the ester substituent and amine produced a range of ionic liquids with low melting points. The products and by‐products were analyzed by spectroscopic and spectrometric techniques in order to get a better mechanistic picture of the dealkylation and formal dearylation observed. For dialkyl H ‐phosphonate diesters, (RO) 2 P(O)H (R=alkyl), the reaction proceeds via direct dealkylation with the reactivity increasing in the order R= i Pr