1,3-Dipolar [3 + 2] Cycloaddition of N-α-Diphenyl Nitrone to the Benzene Ligand in Reductively Activated [Mn(CO)3(η4-C6H6)]

We have established that the η4-benzene ligand in [Mn(CO)3(η4-C6H6)]- undergoes a stepwise cycloaddition reaction with N-α-diphenyl nitrone in a sequence in which the Lewis acid BF3 is first used to induce nucleophilic addition of [Mn(CO)3(η4-C6H6)]- to N-α-diphenyl nitrone. The BF3 can be removed b...

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Bibliographic Details
Published in:Organometallics 2003-07, Vol.22 (14), p.2811-2813
Main Authors: Shao, Li, Geib, Steven J, Badger, Paul D, Cooper, N. John
Format: Article
Language:English
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Summary:We have established that the η4-benzene ligand in [Mn(CO)3(η4-C6H6)]- undergoes a stepwise cycloaddition reaction with N-α-diphenyl nitrone in a sequence in which the Lewis acid BF3 is first used to induce nucleophilic addition of [Mn(CO)3(η4-C6H6)]- to N-α-diphenyl nitrone. The BF3 can be removed by protonation to give the neutral intermediate [Mn(CO)3{η5-C6H6CHPhN(Ph)OH}], which can be cyclized by addition of excess KH and PPNCl to drive ring closure and form containing an isoxazolidine ligand that is the [3 + 2] cycloaddition product of the nitrone with benzene.
ISSN:0276-7333
1520-6041
DOI:10.1021/om030263c