Relative Velocities of Reaction of Alcohols with Phenyl Isocyanate

Davis, Tenney L.; Farnum, James McC.

doi:10.1021/ja01319a035

Cited by 48 publications

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“…This result is consistent with the significantly lower reactivity of isocyanates towards tertiary alcohols. 20 However, employing tert -butanol as the solvent afforded the desired tert-butylcarbamates in 60 - 94% yield (Table 2). …”

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confidence: 99%

Palladium-Catalyzed Synthesis of N-Aryl Carbamates

et al. 2013

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An efficient synthesis of aryl carbamates was achieved by introducing alcohols into the reaction of palladium-catalyzed cross-coupling of ArX (X = Cl, OTf) with sodium cyanate. The use of aryl triflates as electrophilic components in this transformation allowed for an expanded substrate scope for direct synthesis of aryl isocyanates. This methodology provides direct access to major carbamate protecting groups, S-thiocarbamates, and diisocyanate precursors to polyurethane materials.

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confidence: 99%

Palladium-Catalyzed Synthesis of N-Aryl Carbamates

et al. 2013

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“…By monitoring the progress of a reaction mixture of the epoxy resin and TDI (1:1 molar ratio), after the same period and conditions, 40% of free NCO groups were detected. These results indicate that, although slower than the reaction between HTPB and TDI, 8 a reaction between secondary OH groups of ER and TDI also occurs. The FTIR spectrum for this last reaction mixture showed the typical absorption band of C O of urethane, thus confirming the above supposition.…”

Section: Reaction First Stepmentioning

confidence: 77%

Hydroxy‐terminated polybutadiene toughened epoxy resin: Chemical modification, microstructure, and impact strength

et al. 2002

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ABSTRACT:The toughening of the epoxy resin diglycidyl ether of bisphenol A with hydroxy-terminated polybutadiene (HTPB) was investigated. A chemical link between the elastomer and the epoxy resin was promoted employing tolylene diisocyanate (TDI). In the first step, HTPB and TDI (in excess) reacted forming urethane links, and after increasing the temperature and adding a catalyst, TDI-HTPB reacted with epoxy resin forming oxazolidone links. The reactions were followed by FTIR and chemical analysis. The final cured materials contained up to 10 phr of elastomer. Impact resistance increased with elastomer concentration up to 5 phr of HTPB, which was present as rubber particles with average diameter ranging from 1 to 4 m. Higher concentrations of HTPB resulted in larger particles and gave lower impact values. The overall results have shown that it is possible to obtain, with the process employed, an impact resistance increase of 100% with the use of HTPB as a toughening agent for the epoxy resin.

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“…2. o R -N = C = 0 + HA ► RNH-C-A (2) Some of these products are stable, while others can be decomposed easily to the starting material or other products. 2. o R -N = C = 0 + HA ► RNH-C-A (2) Some of these products are stable, while others can be decomposed easily to the starting material or other products.…”

Section: Introductionmentioning

confidence: 99%

N-Carbamates (Urethanes)

1971

Organic Chemistry: A Series of Monographs

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Relative Velocities of Reaction of Alcohols with Phenyl Isocyanate

Cited by 48 publications

References 0 publications

Palladium-Catalyzed Synthesis of N-Aryl Carbamates

Palladium-Catalyzed Synthesis of N-Aryl Carbamates

Hydroxy‐terminated polybutadiene toughened epoxy resin: Chemical modification, microstructure, and impact strength

N-Carbamates (Urethanes)

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