110355-49-2Relevant 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.
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.
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
