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2005
Rearrangements
O 0140
Unexpected Smiles Rearrangement During Borane Reduction of 2-Aryloxy— 2-Nitrophenols (I) spontaneously undergo an unex32- 054 -2-methylpropionamides.
pected Smiles rearrangement during alkylation with 2-bromo-2-methylpropionamide
(VIII) in the presence of Cs2CO3 [→(IX)]. Upon reduction of 2-aryloxy-2-methylpropionamides, readily obtained form nitrophenols (I), with borane dimethylsulfide complex, a Smiles rearrangement is observed as well [→(VI)]. — (BUCHSTALLER*,
H.-P.; ANLAUF, U.; Synthesis 2005, 4, 639-643; Med. Chem. Res. Lab., Merck
KGaA, D-64271 Darmstadt, Germany; Eng.) — D. Singer
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