Scavenge-ROMP-filter: a facile strategy for soluble scavenging via norbornenyl tagging of electrophilic Reagents

Joel D Moore; Andrew M Harned; Julia Henle; Daniel L Flynn; Paul R Hanson

doi:10.1021/ol0257880

Scavenge-ROMP-filter: a facile strategy for soluble scavenging via norbornenyl tagging of electrophilic Reagents

Org Lett. 2002 May 30;4(11):1847-9. doi: 10.1021/ol0257880.

Authors

Joel D Moore¹, Andrew M Harned, Julia Henle, Daniel L Flynn, Paul R Hanson

Affiliation

¹ Department of Chemistry, University of Kansas, 1251 Wescoe Hall Drive, Lawrence, Kansas 66045-7582, USA.

PMID: 12027629
DOI: 10.1021/ol0257880

Abstract

[reaction: see text] 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.

Publication types

Research Support, U.S. Gov't, Non-P.H.S.
Research Support, U.S. Gov't, P.H.S.

MeSH terms

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

Substances

5-norbornene-2-methanol
Alcohols
Amines
Free Radical Scavengers
Indicators and Reagents
Norbornanes
Polymers
Solvents
Methanol