Oxidation of alkylcatecholboranes with functionalized nitroxides for chemical modification of cyclohexene, perallylated polyglycerol and of poly(butadiene)
The present communication reports on the synthesis of alkoxyamines by hydroboration of olefins with catecholborane and subsequent oxidation by using nitroxides. Oxidation occurs via a radical process and the intermediately formed C-radicals are trapped by the nitroxides to form the corresponding alkoxyamines. If functionalized nitroxides are used, the method allows incorporation of interesting functional moieties via this approach. The novel method is applied for chemical modification of cyclohexene as a test substrate. More importantly, it is also shown that the reaction sequence can be used for chemical modification of macromolecules containing multiple double bonds. This is documented by successful functionalization of poly(butadiene) and of perallylated polyglycerol. Functionalized poly(butadiene)s can be prepared by a reaction sequence comprising olefin hydroboration and nitroxide induced oxidation to give poly(alkoxyamines). If the nitroxide is charged with aninteresting functional moiety such as a sugar derivative or a polyethylene glycol tail, the trapping process delivers the corresponding functionalized chemically modified poly(olefins) in a one-pot process.
Wagner, Christine B.,Studer, Armido
supporting information; experimental part
p. 5782 - 5786
(2011/01/12)
Non-migrating 1-hydrocarbyloxy hindered amine derivatives as polymer stabilizers
1-Hydrocarbyloxy substituted hindered amine compounds which also contain a reactive functional group such as hydroxy, amino, oxirane or carboxyl can be chemically attached to selected polymer substrates by condensation reactions to give polymers containing a chemically-bonded, non-migrating stabilizer having excellent stabilization efficacy for protecting said polymer substrate from the adverse effects of actinic light.
Hindered amines based on various 2,2,6,6-tetraalkylated nitrogen-containing heterocyclic moieties wherein the hindered nitrogen atom on the ring is substituted with OR1 substituents and the 4-position of the ring is substituted with a variety of groups, are effective as light stabilizers in diverse substrate systems.
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(2008/06/13)
Process for preparing N-hydrocarbyloxy derivatives of sterically hindered amines
N-hydrocarbyloxy compounds of the formula STR1 where E1, E2, E3 and E4 are independently an organic radical so that the carbon atoms to which they are attached are each a quaternary carbon, R is a hydrocarbon ra
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(2008/06/13)
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