1.2- Propanediol cyclic carbonate

Propanedicarboxylic acid, gl4 Propanedioic acid, m3 1,2-Propanediol cyclic carbonate, p230 Propanenitrile, p215... 

The complex is soluble in N, N-dimethylformamide and propylene carbonate (1,2-propanediol cyclic carbonate), slightly soluble in acetone and dichloro-... 

Propylene carbonate 0 60 P MeCI 1,2-Propanediol cyclic carbonate for gases, hydrocarbons... 

Carbonic acid, cyclic propylene ester cyclic methylethylene carbonate cyclic propylene carbonate 4-methyl-2-oxo-l,3-dioxolane 1,2-propanediol cyclic carbonate 1,2-propylene carbonate. 

Propanediol carbonate 1,2-Propanediol cyclic carbonate 1,2-Propanediyl carbonate ... 

Prop carb propylene carbonate 1,2-propanediol cyclic carbonate... 

Synonyms Carbonic add, cyclic propylene ester Carbonic acid, 1,2-prepylene glycol ester 1,3-Carbonyl dioxypropane Cydic methylethylene carbonate Cyclic propylene carbonate Cyclic 1,2-propylene carbonate 1,3Dioxolan-2-one, 4-methyl Dipropylene carbonate 4-Methyl-1,3-dioxolan-2-one 1-Methyl ethylene carbonate 1,2-Propanediol carbonate 1,2-Propanediol cyclic carbonate 1,2-Pro-panediyl carbonate 1,2-Propylene carbonate Propylene glycol cyclic carbonate Classification Organic compd. carbonic add ester Empiricai C4H5O3... 

Cyclic carbonates of 1,3-propanediols yield thietanes when treated with thiocyanate ion and heated until carbon dioxide is evolved. Yields vary from 3 to 63%, the yield being greater for 3,3-disubstituted thietanes, as illustrated in the synthesis of the spirothietane, 44. Oxetanes are formed as byproducts in... 

The initial synthesis of the SOCM monomer was attempted via the reaction of l-methacryloxy-2,3-propanediol with dibutyltin oxide followed by treatment with the cyclic carbonate 5. However, this process failed to provide any significant quantity of the chloromethyl-methacrylate-substituted intermediate. If this route had been successful, the final SOCM monomer would have been comprised solely of the spiro-fused five-membered rings (3a). Instead, the synthesis of SOCM as shown in Figure 3 yielded a mixture of the 5-5 and 5-6-membered ring systems (3a and 3b, respectively). Each of these different structural isomers is also further subdivided into a pair of syn and anti diastereomers as shown in Figure 6. The complex eutectic mixture which results is a liquid of low viscosity that is well suited for use as a diluent and wetting agent. 

Scheme 11 Synthesis of six-membered cyclic carbonate from 1,3-propanediol and ethyl chloroformate.

Scheme 12.6 Cyclic carbonates and dicarbonate monomers derived from a,(o-diols (1—8), 2,2-disubstituted 1,3-propanediols (9-15) and 2,2-spiro-l,3-propanediols (16-20).

Lipase CA catalyzed the polymerization of cyclic dicarbonates, cyclobis (hexamethylene carbonate) and cyclobis(diethylene glycol carbonate) to give the corresponding polycarbonates [105]. The enzymatic copolymerization of cyclobis(diethylene glycol carbonate) with DDL produced a random ester-carbonate copolymer. As to enzymatic synthesis of polycarbonates, reported were polycondensations of 1,3-propanediol divinyl dicarbonate with 1,3-propanediol [110], and of diphenyl carbonate with bisphenol-A [111]. 

We have systematically examined the facility with which DTPP promotes the cyclodehydration of simple diols to cyclic ethers 1,3-propanediol (1) - oxetane (2) (2-5%) 1,4-butanediol (3) te-trahydrofuran (4) (85%) 1,5-pentanediol (5) - tetrahydropyran (6) (72%) 1,6-hexanediol (7) - oxepane (8) (55-68%). Increased alkyl substitution at the carbinol carbon s gnificantly diminishes the facility for cyclic ether formation. For example, a mixture of meso- and d, 1 —2, 6-heptanediol gave only 6-10% of the cis- and trans-2,6-dimethyltetrahydropyrans when treated with DTPP. While diol 1 resists cyclodehydration with DTPP to oxetane, some 2,2-di-substituted 1,3-propanediols are readily converted to the appropriate oxetanes [e.g., 2-ethyl-2-phenyl-l,3-propanediol -> 3-ethyl-3-phenyloxetane (78%)]. 

Resolution by transesterification. Using vinylic acetates to esterify allyl alcohols, propargyl alcohols, 2-phenylthiocycloalkanols, a-hydroxy esters," methyl 5-hydroxy-2-hexenoates, and 2-substituted 1,3-propanediols, the enantioselective esterification provides a means of separation of optical isomers. Vinyl carbonates are also resolved by lipase-mediated enantioselective conversion to benzyl carbonates. Other esters that have also been used in the kinetic resolution include 2,2,2-tri-fluoroethyl propionate. There is a report on a double enantioselective transesterification" of racemic trifluoroethyl esters and cyclic meso-diols by lipase catalysis. 

As shown in Figure 14.1b two maximum decomposition temperatures are observed corresponding to the two different decomposition steps chain scission at 232 °C and unzipping at 251 °C. The final pyrolysates are not carbon dioxide and propylene oxide, but cyclic propylene carbonate and 1,2-propanediol. 

Reaction with Di- and Polyols. Although intermolecular dehydration between two molecules of alcohols to afford acyclic ethers usually does not occur with the DEAD-TPP system, intramolecular cyclization of diols to produce three to seven-membered ethers is a common and high yielding reaction. Contrary to an early report, 1,3-propanediol does not form oxetane. Oxetanes can be formed, however, using the trimethyl phosphite modification of the Mitsunobu reaction. The reaction of (5)-1,2-propanediol and ( )-l,4-pentanediol with DEAD and TPP affords the corresponding cyclic ethers with 80-87% retention of stereochemistry at the chiral carbon, while (5)-phenyl-1,2-ethanediol affords racemic styrene oxide. In contrast to the reaction of the same 1,2-diols with benzoic acid (eq 4), oxyphos-phonium salts (25a) and (25b) have been postulated as key intermediates in the present reaction (eq 20). ... 

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