Polyfunctional methanes are often found in biomolecules, such as amino acid and lactic acid. Thus, development of their synthetic method is important for exploring medicine and biocompatible materials. In this review, a novel synthetic method of polyfunctional methanes using diethylmesoxalate (DEMO) and N-acylimine as key electrophiles was described. The high electrophilicity of both compounds facilitates addition reaction by versatile nucleophiles. Indeed, DEMO reacted with less nucleophilic acid amide to afford N,O-hemiacetal. N-Acylimine can be generated in situ by O-acylation of the N,O-hemiacetal followed by treatment with base. A reaction of N-acylimine with various kinds of nucleophile such as pyrrole, indole, amine, and acid amide smoothly proceeded. By the sequential reactions, polyfunctional methanes bearing diester moiety, acylamino group, and an additional substituent could be synthesized. Unnatural amino acid derivatives were successfully synthesized by hydrolysis and subsequent decarboxylation of the 1,3-diester moiety.

Polyethyleneglycol 12 mol / polydimethylsiloxane co-polymer (PEG-12 dimethicone) is a type of polyether modified silicone (PEMS), which can form a lamellar liquid crystalline phase, and is widely used in cosmetics. The structural changes of PEG-12 dimethicone caused by water evaporation as well as shear flow were evaluated using simultaneous measurements of rheology and small angle neutron scattering (Rheo-SANS) and neutron reflectometry (NR). In bulk, a reorientation of plate-like lamellar structures were observed and the neutral orientation was the most favorable at high PEG-12 dimethicone concentrations (≥ 36 wt%). However, lamella-to-vesicle transitions were hardly observed. It is also important to understand the static and dynamic adsorption processes of surfactants on a substrate and the structure of the adsorbed dried film, as that are key factors that control function and properties of the formed film. PEG-12 dimethicone turned out to form a bi-layer on a hydrophilized Si-wafer in a similar manner to that in bulk though the structure had a certain level of roughness.