Aryl substituted oxazolinyloxiranes 1a-g have been found to undergo smooth isomerization into oxazolinyl substituted aryl alkanones 2a-g upon treatment with LDA in Et2O at -98°C, warming to room temperature and quenching with satd aq. NH4Cl. A mechanism involving an oxazoline-assisted ortho lithiation of the aryl group (cis to the oxazoline system) of oxiranes 1 is proposed.
An Unexpected Base-Promoted Isomerization of Oxazolinyl Oxiranes: Synthesis of Oxazolinylaryl Alkanones
PERNA, FILIPPO;CAPRIATI, Vito;LUISI, Renzo
2002-01-01
Abstract
Aryl substituted oxazolinyloxiranes 1a-g have been found to undergo smooth isomerization into oxazolinyl substituted aryl alkanones 2a-g upon treatment with LDA in Et2O at -98°C, warming to room temperature and quenching with satd aq. NH4Cl. A mechanism involving an oxazoline-assisted ortho lithiation of the aryl group (cis to the oxazoline system) of oxiranes 1 is proposed.File in questo prodotto:
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