Addition reactions of imenes

Abstract

Imenes most readily add amines and other nucleophilic reagents, such as water, alcohols, mercaptans, hydrogen sulphide, hydrocyanic add. Bismethylsulphonyl-N-methylimene, which was studied more extensively, proved to possess not only electrophilic but also nudeophilic properties.Thus it adds HCl and can be applied in the Friedel-Crafts reaction.In our previous publication 1) it was shown that imenes possess a pronounced addition power towards water. With the aid of this property it was easy to distinguish the imene from the accompanying carbo-methylation product in the case of phenylsulphonyl-methylsulphonyl-acetonitrile, reacting with diazomethane.

Ketene imines

“…As an extension of the photochemical cycloaddition of aldehydes and ketones with olefins, they investigated the photochemical cycloaddition of carbonyls with 18 (equation 11). The results were most (11) Marvin W. Barker …”

“…Staudinger's early work on the reaction of ketene imines with oxygen showed that high temperatures were necessary for reaction; however, Barker and Perumal have shown that reaction between oxygen and ketene imine occurs rapidly at room temperature if copper (11) chloride is present5 *. The ketene imines studied were diphenylketene N-psubstituted phenylimines and the products of the reaction were benzophenone, aryl isonitrile and aryl isocyanate (equation 34).…”

Rearrangement of the 1,2,2-Triphenylethyl Radical

“…The results of the decarbonylation may be interpreted in terms of the following steps36 (eq. [2][3][4][5][6][7][8][9].…”

Synthese und Reaktionen der Ketenimine

“…Ph\ ,C=C=N 0 + (H5C20),P-00 I 1 H5C2 0 (14) Vor kurzem synthetisierte R~u s c h~~~ antistatisch wirksame Bis( trifluormethy1)keten-N-alkylimine (17) aus Bis(trifluor-methy1)thioketen und Dialkylschwefeldiimiden (16), die formal als Ylide anzusehen sind.…”