Reactions of diphenyl- and diethylphosphinodithioic acids with N-alkyl-2-haloaldimines in the synthesis of new P,S- and N,P,S-containing organic compounds
- Authors: Khairullin R.A.1, Gazizov M.B.1, Kirillina Y.S.1, Bashkirtseva N.Y.1
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Affiliations:
- Kazan Research Technological University
- Issue: Vol 87, No 10 (2017)
- Pages: 2313-2319
- Section: Article
- URL: https://journals.rcsi.science/1070-3632/article/view/221408
- DOI: https://doi.org/10.1134/S1070363217100115
- ID: 221408
Cite item
Abstract
Diphenyl- and diethylphosphinodithioic acids, unlike the stronger О,О-dialkyl phosphorodithioic acids, react with N-alkyl-2-chloroaldimines at a 1: 1 ratio, following two pathways: nucleophilic substitution of chlorine in the primary salt by the phosphinothioylthio group and reduction of the cation of the primary salt on the C–Cl bond. Nucleophilic substitution contributes more in the case of the stronger diphenylphosphinodithioic acid, as well as in the case of a large excess of the starting chlorimine. N-Alkyl-2-bromoaldimines react only by a single pathway, specifically, reducing the cation of the primary iminium salt on the C–Br bond. New iminium salts were synthesized and converted into the corresponding aldehydes and imines. The aldehydes synthesized were converted into acetals and five-membered heterocyclic compounds.
About the authors
R. A. Khairullin
Kazan Research Technological University
Email: mukattisg@mail.ru
Russian Federation, ul. K. Marksa 68, Kazan, Tatarstan, 420015
M. B. Gazizov
Kazan Research Technological University
Author for correspondence.
Email: mukattisg@mail.ru
Russian Federation, ul. K. Marksa 68, Kazan, Tatarstan, 420015
Yu. S. Kirillina
Kazan Research Technological University
Email: mukattisg@mail.ru
Russian Federation, ul. K. Marksa 68, Kazan, Tatarstan, 420015
N. Yu. Bashkirtseva
Kazan Research Technological University
Email: mukattisg@mail.ru
Russian Federation, ul. K. Marksa 68, Kazan, Tatarstan, 420015