61783-80-0Relevant academic research and scientific papers
Preparation of Propargylic Sulfinates and their [2,3]-Sigmatropic Rearrangement to Allenic Sulfones
Tata, Rama Rao,Hampton, Carissa S.,Harmata, Michael
supporting information, p. 1232 - 1241 (2017/04/11)
The scope of the [2,3]-sigmatropic rearrangement of propargylic sulfinates to allenic sulfones by silver catalysis was expanded. A series of new propargylic sulfinate esters was generated from a variety of aromatic and heteroaromatic sulfonyl chlorides an
Additions of Organocopper Reagents and Heteroatom Nucleophiles to l-Phenylseleno-2-(p-toluenesulfonyl)ethyne. Preparation of Vinyl and Allenic Sulfones and Formation of Michael, Anti-Michael, and Rearrangement Products
Back, Thomas G.,Bethell, Richard J.,Parvez, Masood,Wehrli, Daniel
, p. 7908 - 7919 (2007/10/03)
l-Phenylseleno-2-(p-toluenesulfonyl)ethyne (4) was produced nearly quantitatively from p-(toluenesulfonyl)ethyne and benzeneselenenyl chloride. It undenvent stereo- and regioselective synadditions of organocopper reagents RCu(CN)Li to the β-position of th
1-(Phenylseleno)-2-(p-toluenesulfonyl)ethyne. A Novel Acetylenic Sulfone That Undergoes Normal and Anti-Michael Nucleophilic Additions
Back, Thomas G.,Wehrli, Daniel
, p. 4737 - 4740 (2007/10/02)
1-(Phenylseleno)-2-(p-toluenesulfonyl)ethyne (3) was prepared from p-toluenesulfonylethyne and benzeneselenenyl chloride in the presence of triethylamine.It undergoes sequential conjugate addition and substitution of the selenium moiety with higher orded
Preparation of Allenic Sulfones and Allenes from the Selenosulfonation of Acetylenes
Back, Thomas G.,Krishna, M. Vijaya,Muralidharan, K. Raman
, p. 4146 - 4153 (2007/10/02)
β-(Phenylseleno)vinyl sulfones 2 are readily obtained from the free-radical selenosulfonation of acetylenes.Compounds 2 isomerize to allyl sulfones 4 under base-catalyzed conditions in nearly quantitative yield, with high stereoselectivity favoring the Z configuration.Allyl sulfones 4 afford generally high yields of allenic sulfones 1 when subjected to oxidation with m-chloroperbenzoic acid or tert-butyl hydroperoxide, followed by selenoxide syn-elimination.The sulfone-stabilized anion intermediates in the isomerizations of 2 to 4 can be alkylated, deuterated,or silylated in the α-position prior to oxidation, providing allenic sulfones with an additional α-substituent.In some cases, spontaneous elimination of the phenylseleno group occurred, producing the allenic sulfone without the need for an oxidation step.Desulfonylation of allyl sulfones 4f, 4c, and 25 with sodium amalgam afforded vinyl selenides that were converted to allenes in moderate to good yields by oxidation-elimination.The copper catalyzed coupling of allyl sulfones 4 with Grignard reagents comprises an alternative route to vinyl selenide precursors of allenes.These procedures permit the synthesis of various α- and γ-substituted allenic sulfones and allenes from acetylenes.
