Journal
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2
Volume -, Issue 1, Pages 169-173Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/a903659h
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n-Decyl phosphate, as the mono benzyltrimethylammonium salt 1, is readily acetylated by 2,4-dinitrophenyl acetate, 2, in dry acetonitrile (MeCN). Reaction is very strongly inhibited by H2O, and acyl phosphate, 3, is not detected with > 20 vol% H2O. In these aqueous media ester 2 is hydrolyzed, probably with general-base catalysis by 1, and the acyl phosphate is also slowly hydrolyzed. Potassium dihydrogenphosphate is slowly acetylated by 2, in moist MeCN in the presence of [18]-crown-6 in heterogeneous conditions, but the yield of acetyl phosphate decreases sharply with > 10 vol% H2O. Sodium n-decyl phosphate is also acetylated by 2 in dry MeCN in the presence of [15]-crown-5. These acetylations in anhydrous media model enzymic-mediated formation of acyl and other labile phosphates.
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