2-Cyanoacrylates in the conjugate addition of trifluoroacetic acid and nucleophilic reagents |
| |
Authors: | G D Kolomnikova T O Krylova I V Chernoglazova P V Petrovskii Yu G Gololobov |
| |
Institution: | (1) A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 ul. Vavilova, 117813 Moscow, Russian Federation |
| |
Abstract: | 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.Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 7, pp. 1245–1247, July, 1993. |
| |
Keywords: | nucleophiles conjugate addition thiourea trifluoroacetic acid phosphines phosphites 2-cyanoacrylates |
本文献已被 SpringerLink 等数据库收录! |
|