TY  - JOUR
PY  - 2009//
TI  - Suicide nucleophilic attack: reactions of benzohydroxamate anion with bis(2,4-dinitrophenyl) phosphate
JO  - Journal of organic chemistry
A1  - Orth, Elisa S.
A1  - da Silva, Pedro L. F.
A1  - Mello, Renata S.
A1  - Bunton, Clifford A.
A1  - Milagre, Humberto M. S.
A1  - Eberlin, Marcos N.
A1  - Fiedler, Haidi D.
A1  - Nome, Faruk
SP  - 5011
EP  - 5016
VL  - 74
IS  - 14
N2  - The reaction between the benzohydroxamate anion (BHO(-)) and bis(2,4-dinitrophenyl)phosphate (BDNPP) has been examined kinetically, and the products were characterized by mass and NMR spectroscopy. The nucleophilic attack of BHO(-) follows two reaction paths: (i) at phosphorus, giving an unstable intermediate that undergoes a Lossen rearrangement to phenyl isocyanate, aniline, diphenylurea, and O-phenylcarbamyl benzohydroxamate; and (ii) on the aromatic carbon, giving an intermediate that was detected but slowly decomposes to aniline and 2,4-dinitrophenol. Thus, the benzohydroxamate anion can be considered a self-destructive molecular scissor since it reacts and loses its nucleophilic ability.<p /> <p>Language: en</p>
LA  - en
SN  - 0022-3263
UR  - http://dx.doi.org/10.1021/jo9007354
ID  - ref1
ER  -