3143-02-0Relevant articles and documents
Kinetics and Mechanism for the Alkaline Homogeneous Hydrolysis of 1,1,1-Trimethylolethane Trinitrate
Hoffsommer, John C.,Glover, Donald J.,Burlinson, Nicholas E.
, p. 315 - 321 (1983)
The kinetics for the alkaline homogeneous hydrolysis of 1,1,1-trimethylolethane trinitrate (MTN) in 95percent ethanol-water with sodium hydroxide concentrations between 0.25 and 2.1 M and temperatures between 50.0 and 60.0 degC have been investigated.One mole of MTN was found to react with 3 mol of base and to hydrolize by a series of consecutive and competitive bimolecular and internal cyclization reactions involving three nitrate ester intermediates to form the cyclic alcohol ether 3-methyl-3-oxetanemethanol (AE) as the final major product with only trace amounts of the expected trialcohol 1,1,1-tris(hydroxymethyl)ethane (TA).MTN and its intermediates showed good second-order rate constants for the expression -d(MTN)/dt = k1(MTN) = k2(B-)(MTN), where k1 is the first-order rate constant with excess base, B-.Relative k2 values in 95percent ethanol-water, 95percent methanol-water, and water were found to be 1.0, 0.1, and 0.01, respectively.Hydrolysis kinetics and product formation for each nitrate ester intermediate have been determined, and an overall hydrolysis mechanism for MTN is presented.
A new and versatile synthesis of 3-substituted oxetan-3-yl methyl alcohols
Boyd, Scott,Davies, Christopher D.
supporting information, p. 4117 - 4119 (2014/07/22)
We have developed a novel route for the efficient synthesis of pharmaceutically significant 3-substituted oxetan-3-yl methyl alcohols starting from readily available malonates. The synthesis harnesses the diversity of malonate chemistry and allows access to a range of oxetanes, which exemplifies the versatility of this procedure.
Synthesis and polymerization of alkyl halide-functional cyclic carbonates
Mindemark, Jonas,Bowden, Tim
experimental part, p. 5716 - 5722 (2012/03/26)
To increase the diversity in functional aliphatic polycarbonates, a series of novel chloro- and bromo-functional six-membered cyclic carbonate monomers were synthesized. Despite asymmetry in the monomer functionalities, homopolymerization of the monomers afforded semicrystalline polycarbonates with a high tendency to crystallize from the melt and/or on precipitation from a THF solution. Melting points were found in the 90-105 °C or 120-155 °C range for polymers comprising methyl or ethyl moieties, respectively, in the backbone. The monomers were further copolymerized with trimethylene carbonate to form random copolymers. Even among some of these random copolymers elements of semicrystallinity were found as confirmed by melting endotherms in DSC. The results clearly show that the incorporation of alkyl halide functionalities in aliphatic polycarbonates may lead to materials with a high ability to form crystallites, even in random copolymers, likely driven by polar interactions due to the presence of the halide functionalities.