167959-48-0Relevant academic research and scientific papers
Novel Synthesis of Cyclopropylaminosulfoxonium Salts from (Dimethylamino)phenylsulfoxonium Methylide
Okuma, Kentaro,Sato, Yasunari,Ishii, Toshiro,Ohta, Hiroshi
, p. 2390 - 2392 (1994)
The reactions of (dimethylamino)phenylsulfoxonium methylide with aldehydes gave unusual cyclopropylaminosulfoxonium salts in good yields when 1,8-diazabicycloundec-7-ene (DBU) was used as a base.This ylide reacted with aldehydes to give the corresponding betaines, which resulted in the formation of vinylsulfoxonium salts.The additional ylide reacted with these salts to afford cyclopropylsulfoxonium salts.
Visible-Light-Promoted Remote C-H Functionalization of o-Diazoniaphenyl Alkyl Sulfones
Du, Shaofu,Kimball, Elizabeth Ann,Ragains, Justin R.
, p. 5553 - 5556 (2017/10/25)
Visible-light irradiation of ortho-diazoniaphenyl alkyl sulfones in the presence of Ru(bpy)32+ results in remote Csp3-H functionalization. Key mechanistic steps in these processes involve intramolecular hydrogen atom transfer from Csp3-H bonds to aryl radicals to generate alkyl/benzyl radicals. Subsequent polar crossover occurs by single-electron oxidation of the alkyl/benzyl radicals to carbenium ions that then intercept nucleophiles. We have developed remote hydroxylations, etherifications, an amidation, and C-C bond formation processes using this strategy.
Synthesis of substituted tetrahydrofurans via intermolecular reactions of γ-chlorocarbanions of 3-substituted 3-chloro-propylphenyl sulfones with aldehydes
Brandt, Agnieszka,Wojtasiewicz, Anna,?niezek, Marcin,Makosza, Mieczys?aw
scheme or table, p. 3378 - 3385 (2010/06/20)
Carbanions of 3-substituted-3-chloropropyl phenyl sulfones add to carbonyl groups of aldehydes to produce aldol type adducts that undergo 1,5-intramolecular substitution giving 2,3,5-trisubstituted tetrahydrofurans. The effect of substituents in the 3-pos
New one-step process for the synthesis of functionalized 1,6-dioxaspiro[4,5]decanes
Carretero, Juan C.,Rojo, Javier,Diaz, Nuria,Hamdouchi, Chafiq,Poveda, Ana
, p. 8507 - 8524 (2007/10/02)
β-Phenylsulfonyl dihydrofurans 1 were readily prepared by reduction of α-phenylsulfonyl-γ-lactones with DIBAL-H, followed by dehydration with MsCl-Et3N. Dihydrofurans 1 were deprotonated with n-BuLi and the resulting α-lithiated carbanion reacted with a wide variety of electrophiles. Particularly interesting is its reaction with γ-lactones because it affords 1,6-dioxaspiro[4,5]decanes in good yields in one-step procedure. This new method of synthesis of spiroketals, in non-acid conditions, is thermodynamically controlled and occurs with high stereoselectivity at C-4, C-5 and C-7, but not at C-2.
One-step Synthesis of Functionalized Dioxaspirodecanes from β-Phenylsulfonyl Dihydrofurans and γ-Lactones
Carretero, Juan C.,Diaz, Nuria,Rojo, Javier
, p. 6917 - 6920 (2007/10/02)
A one-step synthesis of differently substituted 1,6-dioxaspirodecanes from readily available starting materials is described.The process is based on the condensation of the α-anion derived from β-phenylsulfonyl dihydrofurans with γ-lactones.The spirocyclization occurs with high stereoselectivity at C-4, C-5 and C-9, but not at C-2.
Stereoselective synthesis of 3-(phenylsulphonyl)-2,5 disubstituted tetrahydrofurans via 5-endo-trig ring-closure reactions
Craig,Smith
, p. 695 - 698 (2007/10/02)
The synthesis and stereoselective 5-endo-trig cyclization reactions of a series of sulphonyl-substituted homoallylic alcohols are reported. Some competing reactions are described, and a model is proposed to account for the observed stereoselectivity.
