Reactions of [alpha]-Chloro-[alpha]-phosphonopropionic Acid Trichloride with Nucleophilic Reagents

Alcoholysis of [alpha]-chloro-[alpha]-phosphonopropionic acid trichloride with allyl and propargyl alcohols was studied. It was found that the reaction proceeded selectively at the carbonyl carbon atom. The reaction of [alpha]-chloro-[alpha]-phosphonopropionic acid trichloride with triethyl phosphit...

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Bibliographic Details
Published in:Russian journal of general chemistry 2020-08, Vol.90 (8), p.1447
Main Authors: Allakhverdieva, G. E, Ismailov, V. M, Mamedov, I. A, Askerov, R. K, Yusubov, N. N
Format: Article
Language:English
Subjects:
Alcohols
Pyridine
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Summary:Alcoholysis of [alpha]-chloro-[alpha]-phosphonopropionic acid trichloride with allyl and propargyl alcohols was studied. It was found that the reaction proceeded selectively at the carbonyl carbon atom. The reaction of [alpha]-chloro-[alpha]-phosphonopropionic acid trichloride with triethyl phosphite yielded [alpha]-methyl-[beta]-diethylphosphatovinylphosphonic acid dichloride. A method was proposed for the synthesis of previously unknown phosphonobarbiturates and of a number of other phosphorus-containing heterocycles via the reaction of [alpha]-chloro-[alpha]-phosphonopropionic acid trichloride with urea or thiourea in the presence of pyridine. In all the cases, complex salts of pyridine with [alpha]-chloro-[alpha]-phosphonopropionic acid were isolated from the aqueous phase and characterized. The reaction of the trichloride with dimethyl sulfoxide involved its sulfur and oxygen atoms.
ISSN:1070-3632
DOI:10.1134/S1070363220080113