New synthetic reactions using sulfone derivatives = 술폰 유도체를 이용한 새로운 합성반응에 관한 연구

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A convenient syntheses of various vinyl sulfones were depicted. The dilithiomethyl phenyl sulfone had been used to prepare the silylated anion by treatment with trimethylsilyl chloride; subsequent condensation with a carbonyl compound gave a vinyl sulfones via the Peterson reaction. And vinyl sulfones were stereoselectively prepared in high yields in a one-pot by the Witting-Horner reaction via phosphorylation of dilithiomethyl phenyl sulfone. Also,. $\alpha$ -methoxy $\alpha$ ,$\beta$ -unsaturated sulfones and $\alpha$ -chloro $\alpha$ ,$\beta$ -unsaturated sulfones were conveniently prepared in high yields using a one-pot Witting-Horner reaction via phosphorylation of dianion of methoxymethyl phenyl sulfone and chloromethyl phenyl sulfone, respectively. Acetylenic sulfones were obtained by the reaction of chloro(phenylsulfonyl) methanephosphonate with aromatic aldehydes in the presence of excess base and the in situ $\beta$ -elimination reaction of enol phosphates which are generated by the reaction of $\beta$ -keto sulfones with diethyl chlorophosphate in THF in the presence on NaH. 3-phenylsulfony 1-2, 5-disubstituted furans were synthesized by the iodine-induced enoletherification of $\alpha$ -allyl substituted $\beta$ -keto sulfones and followed by dehydroiodination and subsequent in situ isomerization of 4, 5-dihydro-5-iodomethylfurans. 2,4-Trnas-substituted $\gamma$ -butyrolactones were obtained in high selectivity by the iodine-induced lactonization of $\alpha$ -phenylsulfonyl-$\gamma$, $\delta$ -unsaturated amides. On the other hand, it had been found that NBS or NCS-induced lactonization of N, N-dimethyl-2-phenylsulfonyl-4-pentenamide gave $\alpha$ -halogenated $\gamma$ -butyrolactones. 2,4-Disubstituted furans were obtained by dehydroiodination and dehydrosulfonylation and subsequent in situ isomerization of 2-iodoalkyl-4-phenylsulfonyltetra-hydrofurans which were prepared from intramolecular iodine-induced etherification of $\alpha$ -phenylsulfonyl...
Oh, Dong-Young오동영
한국과학기술원 : 화학과,
Issue Date
61609/325007 / 000865332

학위논문(박사) - 한국과학기술원 : 화학과, 1991.2, [ v, 141 p. ]

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