91145-94-7Relevant academic research and scientific papers
Phase-transfer catalysed (PTC) reactions of 1,1-dichloro-2-cyanocyclopropane with nucleophiles. Identification of intermediates
Jonczyk, Andrzej,Kocmierowski, Tomasz,Zdrojewski, Tadeusz
, p. 295 - 299 (2007/10/03)
An addition-elimination mechanism for PTC reactions of phenols with 1,1-dichloro-2-cyanocyclopropane (1) is supported by trapping of intermediate cyclopropenes 3 and 5. PTC reactions of 1 with a series of phenols 2a-d, thiophenol (2e), alcohols 2f,g and dithioles 11a,b led to formation of disubstituted cyanocyclopropanes 6a-d, 6e, 6f,g or spiroproducts 12a,b, respectively. Under acidic conditions or thermally, dialkoxycyclopropanes 6f,g or spirane 12a were transformed into alkyl 3-cyanopropionates 10f,g and ketene dithioacetal 13a.
NUCLEOPHILIC SUBSTITUTION OF HALOGEN ATOMS IN gem-DICHLOROCYCLOPROPANES ACTIVATED BY ELECTRON-WITHDRAWING SUBSTITUENTS
Kulinkovich, O. G.,Tishchenko, I. G.,Romashin, Yu. N.
, p. 213 - 216 (2007/10/02)
The reactions of the methyl ester, N,N-dimethylamide, and nitrile of gem-dichlorocyclopropanecarboxylic acid with sodium methoxide and ethoxide take place with opening of the three-membered ring and lead to the correponding derivatives of succinic acid.Methyl and ethyl 3-formyl-2-methylpropionate were obtained from 2,2-dichloro-1-formyl-3-methylcyclopropane under analogous conditions.The reaction of sodium thiophenolate with the functionally substituted gem-dichlorocyclopropanes takes place with retention of the three-membered ring and the formation of the corresponding substituted diphenyl thioacetals of cyclopropanone.
