Several ionene bromides were used as reagents for the displacement of decyl methanesulfonate into 1-bromodecane. They were very reactive when adsorbed by silica gel. The enhanced activities of the ionenes were hardly dependent on their structures and molecular weights but decreased gradually with increasing the amount of ionene adsorbed by silica gel. Ionene chlorides exhibited a similar enhancement of reactivity when adsorbed by silica gel. However, unlike the ionenes, a large increase in activity due to adsorption was not observed with pendant-type polycations such as poly(4-vinylpyridinium bromide) and poly[(4-vinylbenzyl)tributylammonium chloride]. The silica gel-supported ionenes also exhibited excellent catalytic activities for solid–liquid–solid triphase substitution reactions, particularly for the reactions between 1-bromodecane and such inorganic salts as consisted of relatively hard-basic nucleophilic anions.

Sulfopropylation of perfluorooctanamide or its N‐alkyl substituted derivatives gave products which were valuable as anionic surfactants. The amides were prepared by the reaction of ethyl perfluorooctanoate with ammonia orn‐alkyl amines (C1‐C12), and then treated with 1,3‐propanesultone to obtain the desired products. The surfaceactive properties of these compounds were investigated to elucidate the correlation with the chain length of the N‐alkyl group. Thus, generally speaking, the N‐butyl derivative was found to exhibit properties superior to the others.

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The Darzens glycidic ester condensation was undertaken to prepare ethyl /3-phenylglycidate from benzaldehyde in a solid-liquid two-phase system at higher temperature than 100 °C employing anhydrous potassium carbonate as a condensing agent. It has been found that the reaction is accelerated considerably by a catalyst such as crown ether and the glycidic ester can be obtained in excellent yield. Efforts have been made to reveal the effects of reaction conditions, such as the molar ratio of reactants and the amount of catalyst, condensing agent, or solvent, on the yield and the cis/trans isomer ratio of the product. Thus, the present procedure was found to present a valuable improvement in the Darzens condensation of benzaldehyde, but preliminary experiments revealed that a ketone such as acetophenone took part in the reaction with a poor yield (<25%).