The Chlorination of Anilines. Proof of the Existence of an N-Chloro Intermediate

✍ Scribed by Haberfield, Paul; Paul, Denis

• Book ID: 127396096
• Publisher: American Chemical Society
• Year: 1965
• Tongue: English
• Weight: 155 KB
• Volume: 87
• Category: Article
• ISSN: 0002-7863
• DOI: 10.1021/ja00951a052

✦ Synopsis

Stereochemical considerations indicate that four isomers of IIIa or IIIb should exist as a result of different orientations of the aziridine rings with respect to each other.

Reaction of C3 with N-diphenylmethyleneisopropylamine would be expected to produce one allenic product + IV (IV). Evidence for formation of this product is an allenic absorption in the infrared and an m / e peak at 241 in the mass spectrum of the crude reaction mixture.

No products attributable to reaction of monatomic carbon with the imines used were definitely found, though many components appeared in the chromatograms of the crude reaction mixtures. Such products might be expected since reaction of carbon vapor with alkenes leads to formation of spiropentanes.