Capture-ROMP-release: application for the synthesis of O-alkylhydroxylamines.
[reaction: see text] A new capture-ROMP-release method for chromatography-free purification of N-hydroxysuccinimde Mitsunobu reactions is described. The Mitsunobu reaction captures a variety of alcohols onto a norbornenyl N-hydroxysuccinimide monomer. Subjection of the resulting crude reaction mixture to ROM-polymerization generates a polymer that can be precipitated with methanol and filtered from the Mitsunobu byproducts. Treatment of the polymer with hydrazine releases the substrate from the water-soluble polymer, producing a variety of O-alkylhydroxylamines with good purity.
Harned
Andrew M
AM
Department of Chemistry, University of Kansas, 1251 Wescoe Hall Drive, Lawrence, Kansas 66045-7582, USA.
Hanson
Paul R
PR
D006898:Hydroxylamines / Q000138:chemical synthesis* / Q000302:isolation & purification; D009682:Magnetic Resonance Spectroscopy; D011108:Polymers; D013388:Succinimides / Q000302:isolation & purification
D006898:Hydroxylamines; D011108:Polymers; D013388:Succinimides; C001426:N-hydroxysuccinimide