ROMP-generated oligomeric sulfonyl chlorides as versatile soluble scavenging agents.
[reaction: see text] A new method for homogeneous nucleophilic scavenging employing oligomeric sulfonyl chloride (OSC) reagents is described. The method utilizes OSC to rapidly scavenge a variety of amines that are present in excess. The OSC reagents are generated from ROM polymerization of 2-chlorosulfonyl-5-norbornene utilizing the second generation Grubbs catalyst to produce oligomers of varying size as stable, free-flowing powders. Following the scavenging event, these oligomers are precipitated with ethyl acetate 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.
Herpel
Russell H
RH
Lichtsinn
Joy R
JR
Flynn
Daniel L
DL
Hanson
Paul R
PR
D000588:Amines / Q000737:chemistry; D020650:Combinatorial Chemistry Techniques; D019281:Dimerization; D007202:Indicators and Reagents; D009636:Norbornanes / Q000737:chemistry; D011108:Polymers / Q000138:chemical synthesis*; D012995:Solubility; D013441:Sulfinic Acids / Q000138:chemical synthesis*
D000588:Amines; D007202:Indicators and Reagents; D009636:Norbornanes; D011108:Polymers; D013441:Sulfinic Acids; C044255:sulfonyl chloride