Studies on the reactivity of sulfonium salts알콕시 설포늄 염의 반응성에 대한 연구

The reactivity of $\alpha$ -and $\gamma$ -alkoxydimethylsulfonium salts derived from the reaction of saturated aliphatic acetals, $\alpha,\beta$,-unsaturated acetals, and 3,4-dihydro-2H-pyran with dimethyl sulfide in the presence of trimethylsilyl trifluoromethanesulfonate was investigated, and it was found that alkoxysulfonium salts underwent substitution reaction with various nucleophiles such as Grignard reagents, allylsilanes, silyl enol ethers, allyltins, and lithium thioalkoxides, etc. Aryl and alkyl magnesium bromides reacted efficiently with alkoxysulfonium salts at low temperature to affored the corresponding coupled products, whereas vinyl and acetylenyl magnesium bromides were less reactive. With allylsilanes and silyl enol ethers, the reaction of alkoxysulfonium salt was slower than the corresponding Lewis acid catalyzed reaction of acetals. Allyltins and tin enol ethers were reactive but highly unstable O-alkylated products were obtained in the latter case to give unsymmetrical mixed acetals. Lithium thioalkoxides reacted with alkoxysulfonium salts very fast at low temperature to afford the corresponding monothioacetals in good yields.
Advisors
Kim, Sung-Gak(김성각)researcher
Publisher
한국과학기술원
Issue Date
1991
Identifier
67635/325007 / 000891344
Language
eng
Description

학위논문(석사) - 한국과학기술원 : 화학과, 1991.2, [ iv, 62 p. ]

URI
http://hdl.handle.net/10203/32605
Link
http://library.kaist.ac.kr/search/detail/view.do?bibCtrlNo=67635&flag=t
Appears in Collection
CH-Theses_Master(석사논문)
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