Scavenge-ROMP-filter: a facile strategy for soluble scavenging via norbornenyl tagging of electrophilic Reagents.
[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.
Moore
Joel D
JD
Department of Chemistry, University of Kansas, 1251 Wescoe Hall Drive, Lawrence, Kansas 66045-7582, USA.
Harned
Andrew M
AM
Henle
Julia
J
Flynn
Daniel L
DL
Hanson
Paul R
PR
D000438:Alcohols / Q000737:chemistry; D000588:Amines / Q000737:chemistry; D002384:Catalysis; D016166:Free Radical Scavengers / Q000737:chemistry*; D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy; D000432:Methanol / Q000031:analogs & derivatives / Q000737:chemistry*; D009636:Norbornanes / Q000737:chemistry*; D011108:Polymers / Q000138:chemical synthesis; D012997:Solvents
C458280:5-norbornene-2-methanol; D000438:Alcohols; D000588:Amines; D016166:Free Radical Scavengers; D007202:Indicators and Reagents; D009636:Norbornanes; D011108:Polymers; D012997:Solvents; D000432:Methanol