110355-50-5Relevant academic research and scientific papers
Alkylation of 2-Oxy-Substituted 1-Sulfonylallyl and 1-Sulfonylvinyl Anions. New Routes to Functionalized Carbocycles and Dihydrofurans
Padwa, Albert,Bullock, William H.,Dyszlewski, Andrew D.,McCombie, S. W.,Shankar, B. B.,Ganguly, A. K.
, p. 3556 - 3564 (2007/10/02)
Alkylation of the anion derived from 2-phenoxy-3-(phenylsulfonyl)-1-propene proceeds α to the phenylsulfonyl group and affords cyclic products from 1,ω-dihalides.Reaction of the monoalkylated products, in which a suitably positioned olefinic or acetylenic unit is present, with sodium benzenesulfinate-acetic acid gives functionalized acetylcyclopentenes and cyclohexenes via C-C bond formation from the allyl cation-sulfinate ion pair.In the vinyl sulfone series, deprotonation of (E)- or (Z)-2-alkoxyvinyl phenyl sulfones rapidly affords the more stable (E)-lithio derivative, an acetaldehyde anion equivalent which reacts normally with aldehydes, ketones, alkyl halides, and epoxides.The latter process may be effected in an intramolecular fashion.Thus, (E)-(2-phenylsulfonyl)vinyl ethers of 2,3-epoxy alcohols cyclize on treatment with amide bases to afford dihydrofurans whose stereochemistry is fully defined by that of the starting epoxy alcohol.
PREPARATION AND REACTIONS OF A VINYL CARBANION DERIVED FROM AN OXYGENATED VINYL SULPHONE
Simpkins, N. S.
, p. 989 - 992 (2007/10/02)
Addition of nBuLi to 1,1-dimethoxy-2-phenylsulphonylethane results in stereospecific elimination followed by in situ regiospecific metallation of the resulting vinyl sulphone.
Chemical Reactivity and Configurational Properties of Cyclopropyl Carbanions Derived from a Silyl Sulfonyl Substituted Cyclopropane
Padwa, Albert,Wannamaker, M. Woods,Dyszlewski, Andrew D.
, p. 4760 - 4767 (2007/10/02)
3,3-dimethyl-1-(p-tolylsulfonyl)-2-(trimethylsilyl)cyclopropene was prepared by the 1,3-dipolar cycloaddition of 2-diazopropane with p-tolyl 2-(trimethylsilyl)ethynyl sulfone followed by photoextrusion of nitrogen from the resulting 3H-pyrazole.Treatment
CONFIGURATIONAL PROPERTIES AND CHEMICAL REACTIVITY OF MONO AND DIANIONS DERIVED FROM ARYL 2-ALKOXYVINYL SULFONES
McCombie, S. W.,Shankar, B. B.,Ganguly, A. K.,Padwa, Albert,Bullock, William H.,Dyszlewski, Andrew D.
, p. 4127 - 4130 (2007/10/02)
E-2-Alkoxy-1-arylsulfonylethenes are regio and stereospecifically lithiated at C-1 and the resulting species react efficiently with a variety of electrophiles to give synthetically useful products.
