Bulletin of the Chemical Society of Japan
Online ISSN : 1348-0634
Print ISSN : 0009-2673
ISSN-L : 0009-2673
Formation and Reactions of Alkoxydiaminosulfonium Salts
Hiroshi MinatoKentaro OkumaMichio Kobayashi
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1976 Volume 49 Issue 12 Pages 3601-3604


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 SN2-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 t-butyl (20).

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