64489-06-1Relevant articles and documents
Simple and efficient synthesis of the acetylene equivalent (E)-1-benzenesulfonyl-2-(trimethylsilyl)ethylene
Grigg, Ronald,Najera, Carmen,Sansano, Jose M.,Yus, Miguel
, p. 1111 - 1114 (1997)
The acetylene equivalent (E)-1-benzenesulfonyl-2-(trimethylsilyl)ethylene is readily synthesized in a one-pot reaction, in excellent yield under very mild reaction conditions, via iodosulfonylation-dehydroiodination of vinyltrimethylsilane.
Sulfone reagents in organic synthesis. VI. Sulfonyl- and silyl-substituted hydrocarbons as versatile carbanion precursors in organic synthesis
Eisch, John J.,Behrooz, Mohammad,Dua, Suresh K.
, p. 121 - 136 (2007/10/02)
The basic organometallic chemistry of β-silyl-substituted acetylenic, vinylic and alkyl sulfones has been investigated, with attention being given to metallation, carbometallation and the chemical reduction of carbon-carbon unsaturation. 2-Trimethylsilylvinyl and 2-trimethylsilylalkyl sulfones underwent smooth and stereoselective lithiation with RLi on the carbon α to the sulfonyl group. Carbometallation of vinyl sulfones could be achieved with RMgX or LiCuR2, but acetylenic sulfones carbometallated smoothly only with LiCuR2; with RMgX or RLi, these acetylenes underwent alkyldesulfonylation. The utility in synthesis of these metallo derivatives of sulfonyl-silyl-hydrocarbons is discussed and their value in elaborating carbon skeletons is illustrated for the preparation of alkenes, allenes, carbocycles and stereo-defined vinyl sulfones.
Regiocontrolled Synthesis of Mono-, Di, and Trisubstituted Cyclohexenones by Cycloaddition of Vinyl Sulfones to 1-Methoxy-3--1,3-butadienes. Conversion of Alkenes into Effective Dienophilic Reagents
Kinney, William A.,Crouse, Gary D.,Paquette, Leo A.
, p. 4986 - 5000 (2007/10/02)
Cycloaddition of phenyl vinyl sulfone to Danishefky's diene followed by direct ketalization provided 7, a synthon for the 4-(2-cyclohexenyl) anion.Thus, 7 readily undergoes regiospecific γ-alkylation.Ensuing reductive desulfonylation and hydrolysis provides 2-(and 3-)-cyclohexenones efficiently.Zingiberenol, a monocyclic sesquiterpene, was prepared by means of this methodology.Terminal alkenes and cyclic olefins enter into comparable regiocontrolled Diels-Alder addition if they are first subjected to selenosulfonation and oxidation to the vinyl sulfone.Removal of the phenylsulfonyl substituent after condensation provides the adducts which are formally derived from alkylation of the hypothetical C5 anion of 2-cyclohexenone.The scheme can be expanded to include γ-alkylation prior to desulfonylation.By this means, one is able to prepare 4,5-disubstituted 2-(and 3-)cyclohexenones where the nature of the pendant side chains can be widely varied.
