High-load, ROMP-generated oligomeric bis-acid chlorides: design of soluble and insoluble nucleophile scavengers.
[reaction: see text] An efficient strategy for scavenging a host of nucleophiles utilizing an oligomeric bis-acid chloride (OBAC), generated from the ROM polymerization of trans-bicyclo[2.2.1]hept-5-ene-2,3-dicarbonyl dichloride, is described. The reactivity and high load of the OBAC reagent is exploited in the scavenging of amines, alcohols, and thiols that are present in excess following a common benzoylation event. Following the scavenging event, these oligomers can be precipitated with EtOAc and filtered (SiO(2)), leaving benzoylated nucleophiles in excellent yield and purity.
Department of Chemistry, University of Kansas, 1251 Wescoe Hall Drive, Lawrence, Kansas 66045-7582, USA.
Joel D
JD
Moore
Robert J
RJ
Byrne
Punitha
P
Vedantham
Daniel L
DL
Flynn
Paul R
PR
Hanson
D000143:Acids / Q000737:chemistry; D002712:Chlorides / Q000737:chemistry*; D012995:Solubility
D000143:Acids; D002712:Chlorides