Plasmalogens. I. The Synthesis of 1-Alkenyl Ethers of Glycerol^1,2

Condensation Products of Glycerol with Aldehydes and Ketones. 2-Substituted m-Dioxan-5-ols and 1,3-Dioxolane-4-methanols

“…The 2-(l-bromoalkyl)-l,3-dioxolane-4-methanols undergo an interesting reaction when treated with sodium, all (from C3 to C10 inclusive) yielding 3-(alk-lenyloxy)-propane-l,2-diols (96).…”

Reactions of fatty aldehydes with fatty alcohols: Formation of acetals, hemiacetals and alk‐1‐enyl alkyl ethers

“…TLC of the product (Silica Gel G-toluene) showed one spot having an Rf similar to that of the injected acetal but whose IR spectrum was different from that of the acetal. The characteristic vinyl ether doublet around 1660 cm-] indicated to be a mixture of cis and trans isomers (15,16) of the alk-l-enyl alkyl ether. This absorption band was not as strong as that present in the alk-l-enyl methyl ethers (3,4), perhaps due to the fact that -O-CH=CH-group is situated in the center of the molecule.…”

The Chemical Syntheses of Plasmalogens

“…They used a method discovered by Wislicenus (1878) for the preparation of simple alk-l-enyl ethers (for a review of methods for alk-l-enyl ether synthesis, see Shostakovskii et al, 1968). Piantadosi and Hirsch (1961) and Piantadosi et al (1963) showed that the reaction could also be carried out if a free hydroxyl group was present in the molecule when they converted the glycerol acetal (5) into a mixture of the alk-l-enyl ethers (6) and (7). Piantadosi and Hirsch (1961) and Piantadosi et al (1963) showed that the reaction could also be carried out if a free hydroxyl group was present in the molecule when they converted the glycerol acetal (5) into a mixture of the alk-l-enyl ethers (6) and (7).…”