121033-92-9Relevant academic research and scientific papers
An improved synthesis of vinyl- and β-iodovinyl sulfones by a molecular iodine-mediated one-pot iodosulfonationdehydroiodination reaction
Sawangphon, Tassaporn,Katrun, Praewpan,Chaisiwamongkhol, Korbua,Pohmakotr, Manat,Reutrakul, Vichai,Jaipetch, Thaworn,Soorukram, Darunee,Kuhakarn, Chutima
supporting information, p. 1692 - 1707 (2013/05/22)
An improved one-pot method to synthesize vinyl sulfones from unsaturated systems by using molecular iodine/sodium arenesulfinate/sodium acetate as reagents was described. Vinyl sulfones derived from styrene derivatives were generally obtained in good to excellent yields except for those bearing strong electron releasing substituent. Aliphatic alkenes and activated alkenes gave the corresponding vinyl sulfone products in moderate to good yields. Arylacetylenes yielded the respective β-iodovinyl sulfones in good yields while low yield was observed with aliphatic terminal alkyne. The potentials of the method entail simplicity, short reaction time, non-anhydrous reaction conditions, employing inexpensive, non-metallic reagent and integrating two reactions that are commonly accomplished separately into a single operation. Supplemental materials are available for this article. Go to the publisher's online edition of Synthetic Communications to view the free supplemental file. Copyright Taylor & Francis Group, LLC.
Stereoselective synthesis of (E)-alkenyl sulfones from alkenes or alkynes via copper-catalyzed oxidation of sodium sulfinates
Taniguchi, Nobukazu
supporting information; experimental part, p. 1308 - 1312 (2011/07/07)
Alkenyl sulfones can be stereoselectively synthesized from alkenes or alkynes using sodium sulfinates. The reaction can be performed by a copper-catalyzed oxidation of sodium sulfinates in air. The reaction of alkenes gives (E)-alkenyl sulfones via anti addition of sulfonyl cation and elimination process. Furthermore, the employment of alkynes produces (E) β- haloalkenyl sulfones in the presence of potassium halides. Georg Thieme Verlag Stuttgart · New York.
"Syn-Effect" in the Conversion of (E)-Vinylic Sulfones to the Corresponding Allylic Sulfones
Hirata, Takaki,Sasada, Yoshihiro,Ohtani, Takashi,Asada, Takahiro,Kinoshita, Hideki,et al.
, p. 75 - 96 (2007/10/02)
It was found that (E)-vinylic sulfones preferentially afford (Z)-allylic sulfones as kinetically-controlled products by treatment with a base under mild conditions, while (Z)-vinylic sulfones give (E)-allylic sulfones.Such stereochemical relationship was
Stereochemistry of the Conversion of γ-substituted (E)-Vinylsulfones to the Corresponding Allylsulfones. Determination of the Relative Degree of "Syn-Effect"
Inomata, Katsuhiko,Hirata, Takaki,Suhara, Hiroshi,Kinoshita, Hideki,Kotake, Hiroshi,Senda, Hitoshi
, p. 2009 - 2012 (2007/10/02)
The relative degree of "syn-effect" for the γ-substituted vinylsulfones in their conversion to the corresponding allylsulfones with 1,8-diazabicycloundec-7-ene (DBU) was determined by observing E/Z ratios of the resulting allylsulfones as follows:
The Photolysis of p-Tosylhydrazones of Aryl and α,β-Unsaturated Carbonyl Compounds
Bellesia, Franco,Grandi, Romano,Pagnoni, Ugo M.,Trave, Roberto
, p. 1301 - 1309 (2007/10/02)
The ultraviolet irradiation of p-tosylhydrazones of aryl and α,β-unsaturated carbonyl compounds yields azines and sulphones and exhibits a strong solvent effect.Styryl substrates afford α,β-unsaturated sulphones, the shift of the olefinic double bond probably arising through an intermediate azoderivative.The p-tosylhydrazone of benzylideneacetone is to a great extent transformed to the cis isomer.
