The Preparation of Polymeric and Cyclic Urethans and Ureas from Ethylene Carbonate and Amines

Dyer, Elizabeth; Scott, H. G.

doi:10.1021/ja01560a045

Cited by 66 publications

(35 citation statements)

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“…In earlier applications, corrosioninhibiting lead salts or pigments were used as catalyst. 95 Reaction of aliphatic diamines with cyclic carbonates 96 (1,3-dioxolan-2-ones) results in the formation of β-hydroxyalkyl carbamates. 91 The increasing concern about organotin compounds in the environment has led to the replacement of dibutyltin oxide with bismuth compounds.…”

Section: Blocked Isocyanatesmentioning

confidence: 99%

Tin in Catalysis

et al. 2008

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In numerous natural products and synthetic compounds, ester moieties constitute major organic functional groups. Consequently, (trans)esterification reactions are widely applied in industry, 1 e.g. in the synthesis of fatty acid esters, 2,3 of polyesters 4−9 and of macrolides. 10 More specifically, polylactones and polylactides are multipurpose, bio-compatible and -degradable polyesters, which are suitable for biomedical and pharmaceutical applications. 11−14 Tin-based Lewis acids like mono-and dialkyltin compounds 4,15−19 and tetraalkyldistannoxane derivatives 8,20−22 are very efficient catalysts for transesterification reactions under mild conditions. A considerable drawback in the use of these organotin compounds in organic synthesis is the difficulty of their quantitative removal from the reaction mixture, because some organotin compounds are toxic. These limitations to the exploitation of such reagents and/or catalysts in biomedical and pharmaceutical synthesis applications 23,24 have been recently overcome by exploring alternative and less toxic catalysts, and by the improvement of workup procedures of several types of homogeneous organotin catalysts. Otera et al. have described the synthesis and catalytic activity of perfluoroalkyl distannoxanes, which combine the advantages of efficient catalysis based on organotins with fluorous biphasic technology. 21,25 These types of organotin catalysts, being highly soluble in fluorocarbon solvents, provide solutions which become perfectly miscible with the organic reaction phase upon heating. After cooling the reaction mixture, phase separation is observed and the catalyst returns into the fluorous phase, making it easily and repeatedly recyclable. Another strategy to alleviate the aforementioned toxicity issue, involves grafting the organotin reagent onto an insoluble solid support. 26−28 In this way, other types of environmentally friendly organotin catalysts, which can easily be removed from the desired reaction products by simple filtration of the insoluble support to which they are grafted, are being designed. The forecasted deliverables of such systems include improved catalyst recycling ability and a better control

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Section: Blocked Isocyanatesmentioning

confidence: 99%

Tin in Catalysis

et al. 2008

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“…The formation of cyclic compounds [28] (i.e. oxazolidinones 1 or urea derivatives 2 [29]) depends on the reaction temperature, as well as elimination reactions (meaning formation of alcohols and water) [30], which allow the recovery of an oxazolidinone 3 and of a diol 4 (see Scheme 1).…”

Section: Introductionmentioning

confidence: 99%

How to explain low molar masses in PolyHydroxyUrethanes (PHUs)

Besse

Camara

Méchin³

et al. 2015

European Polymer Journal

113

131

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“…Recently, a method for the synthesis of 2 -oxazolidinones and 2 -imidazolidinones from fi ve -membered CCs and β -amino alcohols or 1,2 -diamines using Br − Ph 3 + P -PEG 600 -P + Ph 3 Br − as a homogeneous recyclable catalyst has been described [ Alkylene carbonate may also react with a hydroxoalkylamine to create a cyclization reaction [260] that affords oxazolidinones (Scheme 7.17 ).…”

Section: Reactivity Of Cyclic Alkylene Carbonatesmentioning

confidence: 99%