Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 74, Issue 21, Pages 8254-8260Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo9017638
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- PRONEX
- FAPESC
- FAPESP
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- CAPES
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Mixed micelles of cetyltrimethylammonum bromide (CTABr) or dodecyltrimethylammonium bromide (DTABr) and the alpha-nucleophile, lauryl hydroxamic acid (LHA) accelerate dephosphorylation of bis(2,4-dinitrophenyl)phosphate (BDNPP) over the pH range 4-10. With a 0.1 mole fraction of LHA in DTABr or CTABr, dephosphorylation of BDNPP is approximately 10(4)-fold faster than its spontaneous hydrolysis, and monoanionic LHA(-) is the reactive species. The results are consistent with a mechanism involving concurrent nucleophilic attack by hydroxamate ion (i) on the aromatic carbon, giving an intermediate that decomposes to undecylamine and 2,4-dinitrophenol, and (ii) at phosphorus, giving an unstable intermediate that Undergoes a Lossen rearrangement yielding a series of derivatives including N,N-dialkylurea, undecylamine, Undecyl isocyanate, and carbamyl hydroxamate
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