3 research outputs found
A Novel Stereoselective Preparation of Various Vinyl Sulfide Derivatives Using β-Alkylthioalkenylselenonium Salts
No full textThe treatment of alkynylselenonium salt and various thiophenol derivatives with a catalytic amount
of triethylamine gave β-arylthioalkenylselenonium salts in good yields. The alkenylselenonium salts
thus prepared reacted with nucleophiles such as acetylides, thiolates, and alkoxides to produce
(Z)-β-arylthio-α-functionalized ethenes in high yields. The vinylselenonium salts bearing a hydroxy
group on a β-side chain caused intramolecular cyclization upon treatment with sodium hydride to
produce medium-membered heterocyclic compounds containing sulfur and oxygen atoms. The
reactions giving (Z)-β-arylthio-α-functionalized ethenes would proceed via the formation of
selenurane intermediates followed by the ligand coupling reaction
Chalcogeno−Morita−Baylis−Hillman Reaction of Enones with Acetals: Simple α-Alkoxyalkylation of Enones
No full text1-[2-(Methylsulfanyl)phenyl]prop-2-en-1-one (1)
and the seleno congener (2) reacted with acetals 3 and 21
in the presence of BF3·Et2O to give α-alkoxyalkyl enones 4,
5 and 22, 23 in good yields. When the reaction mixtures were
worked up with a saturated NaHCO3 solution instead of
Et3N, onium salts 6 and 7 were obtained together with 4
and 5. Reactions with cyclic acetal 14 gave α-(β-hydroxyethoxy) enones 15 and 16 accompanied by dimeric products
17 and 18
Chalcogeno−Morita−Baylis−Hillman Reaction of Enones with Acetals: Simple α-Alkoxyalkylation of Enones
No full text1-[2-(Methylsulfanyl)phenyl]prop-2-en-1-one (1)
and the seleno congener (2) reacted with acetals 3 and 21
in the presence of BF3·Et2O to give α-alkoxyalkyl enones 4,
5 and 22, 23 in good yields. When the reaction mixtures were
worked up with a saturated NaHCO3 solution instead of
Et3N, onium salts 6 and 7 were obtained together with 4
and 5. Reactions with cyclic acetal 14 gave α-(β-hydroxyethoxy) enones 15 and 16 accompanied by dimeric products
17 and 18
