T. O. Krylova

A new insertion reaction of phenyl isocyanate

A new reaction of the insertion of phenyl isocyanate into the C-C bond of P-containing zwitterions based on 2-cyanoacrylates was found. A probable mechanism of this reaction has been discussed.

Alkylation of P-containing zwitter-ions based on 2-cyanoacrylates

The interaction of P-containing zwitter-ions based on ethyl 2-cyanoacrylate with methyl iodide, allyl bromide, α-bromoacetophenone, and 1,3-dichloroacetone has been studied. Alkylation occurs at the central carbon atom of the pentade anion.

2-Cyanoacrylates in the conjugate addition of trifluoroacetic acid and nucleophilic reagents

In the presence of trifluoroacetic acid, ethyl 2-cyanoacrylate readily reacts with nucleophilic reagents, such as 2-chloro-1,3,2-benzodioxaphosphole, (EtO)3P, (EtO)2PCl, Ph2PCl, Ph3P, and thiourea. In these reactions the acid proton enters position 2 of the cyanoacrylate, whereas the nucleophilic component enters position 3, in accordance with the electron density distribution in the acrylate. In the absence of trifluoroacetic acid the above reagents, except 2-chloro-1,3,2-benzodioxaphosphole, cause ethyl 2-cyanoacrylate polymerization. The interaction of ethyl 2-cyanoacrylate with 2-chloro-1,3,2-benzodioxaphosphole and trifluoroacetic acid is the first example of a 2-cyanoacrylate taking part in the acid-initiated electrophilic conjugate addition of a weak nucleophile.

Anticholine esterase activity of phosphonium bis-zwitterions based on 2-cyanoacrylates

Phosphonium bis-zwitterions based on bis-2-cyanoacrylates are weak reversible inhibitors of choline esterases with a diverse anticholine esterase effect. This can find use in additional classification of choline esterases.