Formation and reactions of alkoxydiaminosulfonium salts.

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概要

• 論文の詳細を見る

• Ethoxydimorpholinosulfonium tetrafluoroborate and tetraphenylborate were prepared by ethylation of dimorpholino sulfoxide. They were readily hydrolyzed with water but did not react with methanol. In the reactions with nucleophiles, they acted as ethylating agent for β-picoline, triethylamine, diethylamine, methoxide ion, and chloride ion. When dimorpholino sulfide, 1-chlorobenzotriazole, and an alcohol were allowed to react at −80 °C, the main products were an alkyl chloride, dimorpholino sulfoxide, and morpholinium chloride. Alkoxydimorpholinosulfonium chloride was presumed to be the intermediate, which decomposed by an <I>S</I><SUB>N</SUB>2-type nucleophilic attack of chloride ion on the alkyl group. When (+)-2-octanol was used, the 2-chlorooctane formed was of almost completely inverted configuration (enantiomeric excess, 97%). The yield of alkyl chlorides decreased in the order of methyl (80%), isopropyl (51), and <I>t</I>-butyl (20).

• 公益社団法人 日本化学会の論文

著者

• Minato Hiroshi

  Department Of Electrical Engineering And Computer Science Tufts University

• KOBAYASHI Michio

  Department of Chemistry and Biological Science, College of Science and Engineering, Aoyama Gakuin Un

• Okuma Kentaro

  Department Of Chemistry Faculty Of Science Fukuoka University

• Okuma Kentaro

  Department of Chemistry, Tokyo Metropolitan University

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