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Title: Triad thiophosphoryl-mercapto ylide tautomerism. III. Synthesis and structure of (1-(diphenylphosphinothioyl)-acetonyl)triphenylphosphonium salts

Abstract

(1-(Diphenylphosphinothioyl)acetonylidene)triphenylphosphorane was synthesized, and in its protonation phosphonium salts are formed which have an enol structure in the solid state, but exist as an equilibrium mixture of keto and enol forms in solution. The methylation of the phosphorane goes at the oxygen atom of the carbonyl group and at the sulfur atom the thiophosphoryl group, and the S-methylation product undergoes intramolecular Wittig reaction under mild conditions. Hydrogen 1 and phosphorus 31 NMR spectra were analyzed to confirm these findings.

Authors:
; ; ; ;
Publication Date:
Research Org.:
A. N. Nesmeyanov Institute of Organometallic Compounds, Moscow (USSR)
OSTI Identifier:
5387567
Resource Type:
Journal Article
Journal Name:
J. Gen. Chem. USSR (Engl. Transl.); (United States)
Additional Journal Information:
Journal Volume: 56:6; Other Information: Translated from Zh. Obshch. Khim.; 56: No. 6, 1220-1227(Jun 1986)
Country of Publication:
United States
Language:
English
Subject:
37 INORGANIC, ORGANIC, PHYSICAL AND ANALYTICAL CHEMISTRY; 74 ATOMIC AND MOLECULAR PHYSICS; ORGANIC PHOSPHORUS COMPOUNDS; INFRARED SPECTRA; ISOMERIZATION; METHYLATION; NMR SPECTRA; ORGANIC SULFUR COMPOUNDS; ACETONE; CHEMICAL SHIFT; COUPLING CONSTANTS; DOUBLE RESONANCE METHODS; ELECTRONEGATIVITY; HYDROGEN 1; ISOMERS; J-J COUPLING; MOLECULAR STRUCTURE; ORGANIC SOLVENTS; PHOSPHORUS 31; CHEMICAL REACTIONS; COUPLING; HYDROGEN ISOTOPES; INTERMEDIATE COUPLING; ISOTOPES; KETONES; LIGHT NUCLEI; NUCLEI; ODD-EVEN NUCLEI; ORGANIC COMPOUNDS; PHOSPHORUS ISOTOPES; SOLVENTS; SPECTRA; STABLE ISOTOPES; 400201* - Chemical & Physicochemical Properties; 640302 - Atomic, Molecular & Chemical Physics- Atomic & Molecular Properties & Theory

Citation Formats

Aladzheva, I M, Leont'eva, I V, Petrovskii, P V, Mastryukova, T A, and Kabachnik, M I. Triad thiophosphoryl-mercapto ylide tautomerism. III. Synthesis and structure of (1-(diphenylphosphinothioyl)-acetonyl)triphenylphosphonium salts. United States: N. p., 1986. Web.
Aladzheva, I M, Leont'eva, I V, Petrovskii, P V, Mastryukova, T A, & Kabachnik, M I. Triad thiophosphoryl-mercapto ylide tautomerism. III. Synthesis and structure of (1-(diphenylphosphinothioyl)-acetonyl)triphenylphosphonium salts. United States.
Aladzheva, I M, Leont'eva, I V, Petrovskii, P V, Mastryukova, T A, and Kabachnik, M I. 1986. "Triad thiophosphoryl-mercapto ylide tautomerism. III. Synthesis and structure of (1-(diphenylphosphinothioyl)-acetonyl)triphenylphosphonium salts". United States.
@article{osti_5387567,
title = {Triad thiophosphoryl-mercapto ylide tautomerism. III. Synthesis and structure of (1-(diphenylphosphinothioyl)-acetonyl)triphenylphosphonium salts},
author = {Aladzheva, I M and Leont'eva, I V and Petrovskii, P V and Mastryukova, T A and Kabachnik, M I},
abstractNote = {(1-(Diphenylphosphinothioyl)acetonylidene)triphenylphosphorane was synthesized, and in its protonation phosphonium salts are formed which have an enol structure in the solid state, but exist as an equilibrium mixture of keto and enol forms in solution. The methylation of the phosphorane goes at the oxygen atom of the carbonyl group and at the sulfur atom the thiophosphoryl group, and the S-methylation product undergoes intramolecular Wittig reaction under mild conditions. Hydrogen 1 and phosphorus 31 NMR spectra were analyzed to confirm these findings.},
doi = {},
url = {https://www.osti.gov/biblio/5387567}, journal = {J. Gen. Chem. USSR (Engl. Transl.); (United States)},
number = ,
volume = 56:6,
place = {United States},
year = {Thu Nov 20 00:00:00 EST 1986},
month = {Thu Nov 20 00:00:00 EST 1986}
}