38513-02-9Relevant academic research and scientific papers
Mechanistic Aspects of the Palladium-Catalyzed Isomerization of Allenic Sulfones to 1-Arylsulfonyl 1,3-Dienes
Hampton, Carissa S.,Harmata, Michael
, p. 4807 - 4822 (2016/07/06)
When an allenic sulfone is treated under palladium catalysis in the presence of a weak acid, isomerization to a 1-arylsulfonyl 1,3-diene occurs. Investigations of the mechanistic aspects of this isomerization were performed, leading to the mechanism proposed herein. Some further studies of reaction parameters are reported.
Regiodivergent synthesis of 1- and 2-arylsulfonyl 1,3-dienes
Hampton, Carissa S.,Harmata, Michael
supporting information, p. 1256 - 1259 (2014/03/21)
In the course of a study of the alkoxyallylation of allenic sulfones through the use of π-allylpalladium chemistry, we discovered an isomerization of allenic sulfones to arylsulfonyl 1,3-dienes. Under conditions of palladium catalysis in the presence of acids such as acetic acid, allenic sulfones are converted to 1-arylsulfonyl 1,3-dienes. On the other hand, nucleophilic catalysis using triphenylphosphine in the presence of a proton shuttle yields 2-arylsulfonyl 1,3-dienes. Thus, either regioisomer of the arylsulfonyl diene can be prepared at will based on changes in reaction conditions.
Polystyrene-Supported α-Seleno Carbanions: Efficient Reagents for Highly Stereocontrolled Syntheses of Vinylphosphonates and Vinylsulfones
Xu, Wei Ming,Tang, E,Huang, Xian
, p. 2094 - 2098 (2007/10/03)
Polystyrene-supported selenomethyl-phosphonate and polystyrene-supported selenomethyl-sulfonates have been prepared. These novel reagents were treated with LDA (or n-BuLi) to produce polystyrene-supported α-seleno carbanions, which reacted with alkyl halides, followed by stereospecific selenoxide syn-elimination to give E-vinylphosphonates and E-vinylsulfones respectively. And also these novel polymer reagents can be regenerated and reused.
ISOPRENE FUNCTIONALIZATION E/Z-ISOMERISM OF 1-SULFONYL SUBSTITUTED 2-METHYLBUTADIENES
Burger, J. J.,Chen, T. B. R. A.,Waard, E. R. De,Huisman, H. O.
, p. 723 - 726 (2007/10/02)
The isomeric chlorosulfones 3, 4 and 4 are prepared by 1,4-addition of sulfonyl chlorides to isoprene.Dehydrohalogenation affords the corresponding 2- and 3-methylbutadienyl sulfones in a configuration which is dependent on the configuration of the chlorosulfone.Pure Z-2-methylbutadienyl sulfones 1 are obtained by displacement of primary halides by the Z-sulfinate anion 2.The Z-sulfones 1 are isomerized to E/Z-mixtures.The E/Z-mixtures are separated into their components and the configuration of the isomers is established by the NMR-NOE technique.
