7594-43-6Relevant academic research and scientific papers
ASYMMETRIC ENE REACTION CATALYZED BY CHIRAL ORGANOALUMINIUM REAGENT
Maruoka, Keiji,Hoshino, Yorihisa,Shirasaka, Tadashi,Yamamoto, Hisashi
, p. 3967 - 3970 (1988)
The asymmetric ene reaction of prochiral aldehydes with alkenes has been effected by chiral organoaluminium reagent providing optically active homoallylic alcohols in both enantiomeric forms with high enantiomeric purity.
Metalation reactions. XXIV. Metalation of (vinylthio)benzene
Cabiddu, Maria Grazia,Cabiddu, Salvatore,Cadoni, Enzo,Cannas, Rita,Fattuoni, Claudia,Melis, Stefana
, p. 14095 - 14104 (2007/10/03)
The addition of organolithium compounds to (vinylthio)benzene (1) and then an electrophilic quenching followed by a further metalation/electrophilic quenching is a general method to prepare in one pot (alkylthio)benzenes ortho, alpha-substituted with equal or different groups. The direct dimetalation of 1 affords the ortho, alpha-dilithiated species 15 besides other by-products. Starting from 15 it is possible to obtain in one step ortho, alpha-substituted (vinylthio)benzenes and heterocyclic compounds.
Highly stereoselective syntheses of alkenylsilanes and germanes utilizing cyclobutyl ketones
Fujiwara, Tooru,Sawabe, Koichi,Takeda, Takeshi
, p. 8349 - 8370 (2007/10/03)
(E)-Alkenylsilanes were synthesized with high stereoselectivity by the diastereoselective addition of the dimethylphenylsilyllithium to the trans-2-phenylthiocyclobutyl ketones and the Lewis acid-promoted promoted stereospecific ring opening reactions of the resulting cyclobutanemethanol derivatives. (E)-1,5-Disubstituted 1,5-dienylsilanes and germanes were also produced stereoselectively by the similar zinc salt-catalyzed ring opening reaction of α-dimethylphenylsilyl- or α-triethylgermyl-1-[2-(trimethylsilylmethyl)cyclobutane]methanol derivatives.
An efficient synthesis of unsymmetrical dithioacetals from sulfoxides and thiols by the magnesium amide-induced pummerer-type reaction
Kobayashi, Kazuhiro,Kawakita, Masataka,Akamatsu, Hideki,Morikawa, Osamu,Konishi, Hisatoshi
, p. 2645 - 2647 (2007/10/03)
It has been found that the reactions of sulfoxides bearing hydrogen(s) at the α-position (R 1 SOCHR 2R 3: R 1 = alkyl or Ph; R 2 = H, alkyl, or Ph; R 3 = H or Me) with thiols (R 4SH: R 4 = alkyl or aryl) in the presence of the (diisopropylamino)magnesium
Reductive α-substitution of sulfoxides with grignard reagents promoted by a magnesium amide
Kobayashi, Kazuhiro,Yokota, Kouichi,Akamatsu, Hideki,Morikawa, Osamu,Konishi, Hisatoshi
, p. 441 - 443 (2007/10/03)
The reactions of sulfoxides bearing α-hydrogen(s) (RSOCHR1R2: R-alkyl or aryl; R1, R2 = H, alkyl, or aryl) with Grignard reagents (R3MgBr: R3 = Et, Ph, or vinyl) in the presence of the diisopropylaminomagnesium reagent, generated in situ by the treatment of diisopropylamine with the appropriate Grignard reagents in diethyl ether, have resulted in the formation of the corresponding sulfides (RSCR1R2R3) in moderate to good isolated yields.
Reactions of Sulfoxides with Magnesium Amides. Transformations of Sulfoxides into Sulfides, Dithioacetals and Vinyl Sulfides
Kobayashi, Kazuhiro,Kawakita, Masataka,Yokota, Kouichi,Mannami, Tohru,Yamamoto, Koji,et al.
, p. 1401 - 1408 (2007/10/02)
The reactions of sulfoxides with magnesium amides generated in situ from the reaction of ethylmagnesium bromide and seconday amines, such as diisopropylamine (DIPA) or 2,2,6,6-tetramethylpiperidine (TMP) in diethyl ether, were examined.Diaryl sulfoxides were heated with the diisopropylaminomagnesium reagent in diethyl ether to give the corresponding diaryl sulfides in 42-52percent yields.Sulfoxides bearing hydrogens at the α-position only(RSOCH2R1) reacted with the tetramethylpiperidinomagnesium reagent at room temperature to produce the corresponding dithioacetals (RSCHR1SR) in 47-86percent yields.The treatment of sulfoxides bearing hydrogens both at the α-and β-positions (RSOCHR1CHR2R3) with the magnesium amides at room temperature afforded the corresponding vinyl sulfides (RSCR1=CR2R3) in 52-72percent yields accompanying 2.3-27percent yields of the corresponding dithioacetals.The pathways leading to the products involving the formation of the sulfur-stabilized carbonium ion intermediates are discussed.
Synthesis of 1,1-Disubstituted Ethenes by Means of Sequential Cross-Coupling Reactions
Fiandanese, V.,Marchese, G.,Naso, F.,Ronzini, L.
, p. 1034 - 1036 (2007/10/02)
A variety of 1-alkenes are synthesized in 63-91percent yields by means of sequential cross-coupling reactions of Grignard reagents with readily available or commercial starting materials, in the presence of transition-metal catalysts.
A New Syntethic Route to Vinyl Sulfides Utilizing the Reaction of (Phenylthio)carbenes with Nitrile Anions
Harada, Toshiro,Karasawa, Akio,Oku, Akira
, p. 842 - 846 (2007/10/02)
Reactions of nitrile anion (LiCR2R3CN) and (phenylthio)carbenes generated from 1-chloroalkyl phenyl sulfides (R1CH(Cl)SPh) 2a-e by the action of n-BuLi have been shown to be a useful synthetic route to vinyl sulfides (PhSC(R1)=CR2R3) 3a-k (34-91percent).The nucleophilic attack of the nitrile anion on the carbenic species gave the presumed intermediate β-(phenylthio)-β-lithionitrile, which eliminated LiCN to give the expected vinyl sulfides.The application of the present reaction to the synthesis of cyclic vinyl sulfides was successful: the decomposition of the dianion ofω,ω-bis(phenylthio)alkanenitriles (8b, 8c, 11, and 14) affording the corresponding 1-(phenylthio)cycloalkenes (9, 10, 12, and 15) in 12-87percent yields.
MONOTHIOACETALIZATION OF ACETALS USING DIETHYLALUMINIUM THIOPHENOXIDE
Masaki, Yukio,Serizawa, Yuzuru,Kaji, Kenji
, p. 1933 - 1936 (2007/10/02)
Reactions of diethylaluminium thiophenoxide (Et2AlSPh) with acetals of several types, in which acyclic, cyclic, and bicyclic ones are involved, were examined in comparison with the known reaction using thiophenol in the presence of Lewis acid and found to provide a new and efficient method for preparation of monothioacetals.
