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.
Moore
Joel D
JD
Department of Chemistry, University of Kansas, 1251 Wescoe Hall Drive, Lawrence, Kansas 66045-7582, USA.
Byrne
Robert J
RJ
Vedantham
Punitha
P
Flynn
Daniel L
DL
Hanson
Paul R
PR
D000143:Acids / Q000737:chemistry; D002712:Chlorides / Q000737:chemistry*; D012995:Solubility
D000143:Acids; D002712:Chlorides