41654-16-4Relevant articles and documents
Upgrading castor oil: From heptanal to non-isocyanate poly(amide-hydroxyurethane)s
Ruiz,Aghmiz,Masdeu-Bultó,Lligadas,Ronda,Galià,Cádiz
, p. 226 - 234 (2017)
Intensive research has recently been carried out to synthesize non-isocyanate polyurethanes (NIPUs) from five-membered cyclic carbonates and amines as a sustainable route to industrial relevant polyurethanes. Herein, an activated disubstituted cyclic carbonate and methyl ester containing monomer CE was prepared using castor oil based heptanal and CO2. Good results for the catalytic cycloaddition have been obtained using renewable sugar cane bagasse in combination with TBAB, and this system has been shown to be recyclable. A novel poly(amide-hydroxyurethane) (PAHU) was obtained by bulk ring-opening and amidation polymerization of high reactive CE with 1,6-diaminohexane at low temperature and in absence of catalyst. PAHU contains aliphatic pendant moieties allowing its self-assembling into nanoparticles in aqueous solution, showing potential application in catalysis or drug delivery among other applications.
Electron Transfer Profile of Cyclopropanone Acetals in the Nonirradiated Reaction with Tetracyanoethylene, Chloranil, and Dicyanodichlorobenzoquinone
Oku, Akira,Abe, Manabu,Iwamoto, Masaharu
, p. 7445 - 7452 (2007/10/02)
The donor profiles of cyclopropanone acetals 1 and 2 were examined in the reactions with electron acceptors (TCNE, DDQ, chloranil, and 1-cyanonaphthalene).With TCNE under nonirradiating conditions, an exclusive 2 + 2 cycloaddition took place stereospecifically with monosubstituted acetals 1a-c but nonstereospecifically with disubstituted acetals 1d,e.With quinones, a ring-opening of the cyclopropane and its coupling with the quinone took place to give the C (cyclopropane)-O (quinone) adduct 9 (with chloranil) or 10 (with DDQ), the latter of which underwent the elimination of a phenol to produce unsaturated esters 5 and 6.In addition, the intervention of the C (cyclopropane)-C (quinone) adduct 14 (with chloranil) or 15 (with DDQ), both as the precursor of 5 and 6, was also postulated.With 1-cyanonaphthalene, under photolysis, the cis/trans isomerization of 1 and 2 occured.The results provided evidences that cyclopropanone acetals, in general, are prone to function as donors.The mechanism of the reaction with quinones, in particular, was investigated in detail.