- SYNTHESIS AND ALKYLATION OF VINYLSULFINIC ACIDS VIA FLUORIDE CLEAVAGE OF β-TRIMETHYLSILYLETHYL VINYL SULFONES
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A new method for the synthesis of vinylsulfinic acids from aldehydes is described.The homologated vinyl (trimethylsilylethyl)sulfones were synthesized from the corresponding aldehydes by means of the phosphonium salt derived from the chloromethylsulfide o
- Palmer, James T.,Fuchs, P. L.
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p. 233 - 246
(2007/10/02)
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- Reactions of (Aryloxy)oxosulfonium Ylides with Carbonyl Compounds
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Reactions of (aryloxy)oxosulfonium salts with alkyllithium followed by the additon of carbonyl compounds gave β-aryloxy sulfones, β-aroyloxy sulfones, and α,β-unsaturated or β,γ-unsaturated sulfones in 1.4-17.9percent, 1.2-7.2percent, and 4.5-13.5percent yields, respectively.Ylides obtained by treatment of these sulfonium salts with n-BuLi reacted with carbonyl compounds to give betaines, which formed unusual four-membered cyclic alkoxyoxosulfonium salts.The aryloxy anions thus formed attacked β-carbons of these salts to afford β-aryloxy sulfones.The aroyloxy anion that might be formed by autoxidation also attacked β-carbons of these salts to afford β-aroyloxy sulfones.When these anions attacked the α- or γ-protones of these salts, unsaturated sulfones were obtained.This is the first example that the reaction of ylide with carbonyl compounds gave sulfone derivatives via four-membered cyclic alkoxyoxosulfonium salts that were produced by the intramolecular SN2 mechanism.The yields of unsaturated sulfones were raised up to 35-60percent by a one-pot reaction.
- Okuma, Kentaro,Nakanishi, Kazuto,Ohta, Hiroshi
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p. 1402 - 1407
(2007/10/02)
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