Scavenge−ROMP−Filter:  A Facile Strategy for Soluble Scavenging via Norbornenyl Tagging of Electrophilic Reagents

Scavenge−ROMP−Filter:  A Facile Strategy for Soluble Scavenging via Norbornenyl Tagging of Electrophilic Reagents

A new “chemical tagging” method for homogeneous electrophilic scavenging is described. The method utilizes 5-norbornene-2-methanol to scavenge/tag a variety of electrophiles that are present in excess. Once tagging is complete, the crude reaction mixture is subjected to a rapid ROM polymerization ev...

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Veröffentlicht in:Organic letters 2002-05, Vol.4 (11), p.1847-1849
Hauptverfasser: Moore, Joel D, Harned, Andrew M, Henle, Julia, Flynn, Daniel L, Hanson, Paul R
Format: Artikel
Sprache:eng
Schlagworte:
Alcohols - chemistry
Amines - chemistry
Catalysis
Free Radical Scavengers - chemistry
Indicators and Reagents
Magnetic Resonance Spectroscopy
Methanol - analogs & derivatives
Methanol - chemistry
Norbornanes - chemistry
Polymers - chemical synthesis
Solvents
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Zusammenfassung:A new “chemical tagging” method for homogeneous electrophilic scavenging is described. The method utilizes 5-norbornene-2-methanol to scavenge/tag a variety of electrophiles that are present in excess. Once tagging is complete, the crude reaction mixture is subjected to a rapid ROM polymerization event utilizing the second generation Grubbs catalyst. This process yields a polymer that can be precipitated with methanol or ether/hexane, leaving products in excellent yield and purity.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol0257880