Synthesis of sulfur compounds by the aid of vinyl ethers and acetylene. Communication 7. Peculiarities of the reaction of addition, contrary to Markov Nikov's rule, of hydrogen sulfide to butyl vinyl ether

Author(s):  
M. F. Shostakovsky ◽  
E. N. Prilezbaeva ◽  
E. S. Shapiro
Inorganics ◽  
2019 ◽  
Vol 7 (10) ◽  
pp. 121
Author(s):  
Takahashi ◽  
Shimbayashi ◽  
Fujita

The reaction of [(Cp*Ir)2(μ-dmpm)(μ-H)][OTf] (2) [Cp* = η5-C5Me5, dmpm = bis(dimethylphosphino)methane] with 2,3-dihydrofuran gives [(Cp*IrH)2(μ-dmpm){μ-(2,3-dihydrofuranyl)}][OTf] (3) in an isolated yield of 70% via the C–H bond activation at the 5-position of 2,3-dihydrofuran. Complex 3 is slowly converted into [(Cp*Ir)2(μ-dmpm)(μ-C=C(H)CH2CH2OH)][OTf] (4) quantitatively via the proton-mediated C–O bond activation. The reaction of 2 with ethyl vinyl ether gives [(Cp*Ir)2(μ-dmpm)(μ-CH=CH2)][OTf] (5) in the isolated yield of 64% via the successive activation of C–H and C–O bonds.


2005 ◽  
Vol 70 (9) ◽  
pp. 1411-1428 ◽  
Author(s):  
Petr Štěpánek ◽  
Ondřej Vích ◽  
Lukáš Werner ◽  
Ladislav Kniežo ◽  
Hana Dvořáková ◽  
...  

The stereoselectivity of cycloaddition of sugar-containing substituted 1-(thiazol-2-yl)but-2-en-1-ones 1 and vinyl ethers was studied using the achiral vinyl ether/chiral catalyst as well as the chiral vinyl ether/achiral catalyst combinations. It has been shown that Eu(fod)3-catalyzed cycloaddition of oxadienes 1a-1e with the chiral vinyl ethers 9 and 10 affords stereoselectively almost pure cycloadducts 11a-11e and 12a-12e, respectively. The obtained cycloadducts are suitable precursors for the synthesis of α-C-(1→3)-disaccharides, containing 2-deoxy-arabino-hexopyranose moiety of D- or L-configuration.


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