Phosphonic acid → HCID 88799872, compound

Participants

Reaction Steps

It must be presumed that, in the reaction mechanism of this surprising reaction, a four-membered ring intermediate is formed, which is hydrolyzed into the phosphonic acid by water, and that consequently the reaction proceeds in accordance with the following scheme: ##STR6## This reaction mechanism also seems to play a minor part in the reaction of aliphatic primary amines with bis(chloromethyl)phosphinic acid, where it occurs as a troublesome secondary reaction. It has been observed by the applicant for example that, in the reaction of bis (chloromethyl)-phosphinic acid with tert-butylamine in accordance with M. K. Il'ina and I. M. Shermergorn, Bull. Acad. Sci. USSR, 1968, page 1759 (English edition), not only is the desired bis(tert-butylaminomethyl)phosphinic acid described in this reference obtained in 30.4% yield, but also small amounts (3.2%) of tert-butyl-methylaminomethylphosphonic acid of the formula ##STR7## simultaneously result. Likewise, in the reaction of bis(chloromethyl)phosphinic acid with methylamine, a small amount of dimethylaminomethylphosphonic acid

Provenance & Evidence