124089-33-4Relevant academic research and scientific papers
Chalcogeno Morita-Baylis-Hillman Reaction of 2-(Methylchalcogeno)phenyl Vinyl Ketones with Aldehydes, Ketones, and α-Dicarbonyl Compounds
Kinoshita, Hironori,Kinoshita, Sayaka,Munechika, Yukari,Iwamura, Tatsunori,Watanabe, Shin-Ichi,Kataoka, Tadashi
, p. 4852 - 4861 (2003)
Reactions of 2-(methylchalcogeno)phenyl vinyl ketones 1 and 4 with aldehydes 5 were conducted in the presence of BF3·Et 2O. The reaction was quenched by addition of Et3N and gave the Morita-Baylis-Hillman adducts 6-7 in good yields. When the reaction mixture of 1 with 5a was worked up with saturated aqueous NaHCO3, the sulfonium salt 8a was obtained together with 6. Ketones 10, α-diketones, and α-oxo esters 13, which hardly react in the traditional Morita-Baylis-Hillman reaction, similarly reacted with 2-(methylchalcogeno)phenyl vinyl ketones 1 and 4 to give the Morita-Baylis-Hillman adducts 11-12 and 14-15. Selenochromanones 9 and 16 were obtained together with 7 and 15 from reactions of seleno derivative 4, with 5 and 13 as by-products. The formation mechanism for the sulfonium salt syn-trans-8a is discussed. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003.
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.
