80589-07-7Relevant academic research and scientific papers
Stereoselective access to highly substituted vinyl ethers via trans-difunctionalization of alkynes with alcohols and iodine(iii) electrophile
Ding, Wei,Chai, Jinkui,Wang, Chen,Wu, Junliang,Yoshikai, Naohiko
, p. 8619 - 8624 (2020)
A method for the regio- and stereoselective synthesis of highly substituted vinyl ethers via trans-1,2-difunctionalization of alkynes with a cyclic λ3-iodane electrophile (benziodoxole triflate) and alcohols is reported. The reaction tolerates a variety of internal and terminal alkynes as well as various alcohols, affording β-λ3-iodanyl vinyl ethers in good yields with high regio- and stereoselectivities. The benziodoxole moiety of the products can be used as a versatile linchpin for the synthesis of structurally diverse vinyl ethers that are difficult to access by other means.
MESOMERIC ANIONS IX. MECHANISM AND LAWS OF ALKYLATION OF ALKALI-METAL DERIVATIVES OF 2-BENZOYLPROPIONITRILE
Emelina, E. E.,Ershov, B. A.
, p. 1820 - 1825 (2007/10/02)
The quantitative relationship governing the alkylation of ambident nucleophiles (alkali-metal derivatives of 2-benzoylpropionitrile) by alkyl halides RY (R = Me, Et, i-Pr, Y = Cl, Br, I) and methyl p-toluenesulfonate in hexamethylphosphorotriamide and dimethylformamide were investigated.The ratio of the C- and O-alkylation products does not depend on the concentration of the ambident enolate or the nature of the cation; it decreases with increase in the "hardness" of the leaving group of the alkylation agent and with increase in the size of the alkyl group.Conductometric investigation of the conductivity of solutions of the sodium and potassium derivatives of 2-benzoylpropionitrile in dimethylformamide showed that in the range of 0 - 40 deg C they are dissociated to the extent of 40 - 95percent.The methylation rate only depends on the concentration of the "free" anion.The activation parameters were determined, and the mechanism of the process is discussed.
