124089-20-9Relevant academic research and scientific papers
REDUCTION OF SULFONIUM AND SELENONIUM SALTS WITH SAMARIUM DIIODIDE
Kataoka, Tadashi,Iwama, Tetsuo,Shimizu, Hiroshi,Hori, Mikio
, p. 169 - 172 (2007/10/02)
Treatment of sulfonium and selenium salts with 2 equiv of a THF solution of samarium diiodide caused the reductive cleavage of the C-S or C-Se bonds in high yields.The bond cleavage took place regioselectively between the positive sulfur or selenium atom and the carbon atom with an electron-withdrawing group or a vinyl group.Some medium-sized cyclic sulfides or selenides were synthesized by this method.
Synthesis of Medium-Sized Cyclic Sulfides and Selenides by Crosspiece C-X Bond Cleavage of Bicyclic Onium Salts Bearing a Bridgehead Sulfur or Selenium Atom
Kataoka, Tadashi,Iwama, Tetsuo,Tsutsumi, Kazuhiro,Nakamura, Yoshihide,Matsumoto, Harutoshi,et al.
, p. 3153 - 3194 (2007/10/02)
Medium-sized cyclic sulfides 5a-5h and selenides 5i-5k were synthesized by reductive C-X bond cleavage of bicyclic sulfonium 4a-4h and selenonium salts 4i-4k, respectively.Reducing agents used were magnesium metal, sodium borohydride and samarium diiodide.Samarium diiodide reduction of simple sulfonium and selenonium salts 11a-11d, 15-18 was also carried out.Application of this method to the C-S bond cleavage of sulfonium salts 25a and 25b provided sulfur-containing medium-sized lactams 26a and 26b, respectively, in high yields.Treatment of the sulfonium salts 4f and 4g with a base gave an olefinic sulfide 33 and a cyclopropane derivative 31, respectively.The stereochemistry of the sulfonium, 4d and 4e, and selenonium salts, 4j and 4k, is discussed on the basis of the 13C NMR spectral data.
A New Method for Radical Generation: Reductive C-Se or C-S Bond Cleavage of Cyclic Onium Salts
Kataoka, Tadashi,Tsutsumi, Kazuhiro,Kano, Kenji,Mori, Kazuya,Miyake, Miho,et al.
, p. 3017 - 3025 (2007/10/02)
2-Methyl-3,4-dihydro-1H-2-benzoselenopyranium salt (1) was reduced by some metallic reagents or magnesium metal via the single-electron transfer (SET) process to give 2--toluene (2).Magnesium metal was a good SET reducing agent.Some other selenonium or sulphonium salts (7), (14), (22), (27) and (32) were similarly reduced by magnesium.Particularly, sonication accelerated the reductions. ε-Eneselenonium salt (43) was treated with activated magnesium to give a cyclised pyrrolidine derivative (44).
RADICAL C-Se BOND CLEVAVAGE OF SELENONIUM SALTS WITH GRIGNARD REAGENTS OR MAGNESIUM METAL
Hori, Mikio,Kataoka, Tadashi,Shimizu, Hiroshi,Tsutsumi, Kazuhiro
, p. 981 - 984 (2007/10/02)
The reaction of 2-methylisoselenochromanium salt with Grignard reagents afforded the reductive ring-opened product by the single electron transfer (SET) mechanizm, not by the self-decomposition of ?-selenurane.The same reduction was observed in the reaction of the selenonium salt with magnesium metal.Some other selenonium salts were easily reduced by magnesium metal to give ring-opened products.
