Kinetische untersuchungen zur reaktionsfähighkeit von chlormethylgruppen in methylendiphenolen

✍ Scribed by Böhmer, Volker ;Stein, Günter

• Publisher: Wiley (John Wiley & Sons)
• Year: 1984
• Weight: 855 KB
• Volume: 185
• Category: Article
• ISSN: 0025-116X
• DOI: 10.1002/macp.1984.021850205

✦ Synopsis

The chloromethyl derivatives of 16 differently substituted methylenediphenols were synthesized for the first time. To compare their reactivity, the solvolysis in methanol and the aminolysis with an excess of p-nitroaniline in dimethyl sulfoxide were studied kinetically at 25 "C. The rate constants for the methanolysis do not differ very much, beside of the fact that para-chloromethyl derivatives react about 100 times faster than ortho-chloromethyl derivatives.

However, for the aminolysis a large acceleration up to Id was found for compounds having both hydroxyl groups in ortho-position to the methylene bridge. Obviously, the cleavage of the 0-H bond, which occurs in the rate determining step of the aminolysis, is strongly favoured by an intramolecular hydrogen bond between the phenolic hydroxyl groups. a) Fa. Carl Freudenberg, D-694 Weinheim.