Synthesis of O,S-dialkyl hexyl- and cyclohexyl-phosphonothioates

Journal Article · Sun Sep 20 04:00:00 EDT 1987 · J. Gen. Chem. USSR (Engl. Transl.); (United States)

OSTI ID:5099538

Butorina, L S; Zalesova, N N; Nifant'ev, E E; Mastryukova, T A

We developed a new method for the synthesis of phosphonothiolates with hexyl and cyclohexyl groups on the phosphorus atom. As starting compounds we used hexyl- and cyclohexyl-phosphonous acids. By reaction with 2H-hexamethyldisilazane and sulfur they are readily converted into O,O-bis(trimethylsilyl) alkylphosphonothioates. We found that in the reactions of the silyl esters obtained with solutions of alkyl halides successively in alcohol and benzene in presence of triethylamine good yields are obtained (64-65%) of O,S-dialkyl hexyl- and cyclohexyl-phosphonothioates. The O,S-dialkyl hexyl-and cyclohexyl-phosphonothioates were characterized by their elemental analyses and IR and /sup 1/H and /sup 31/P NMR spectra. The PMR spectra contain multiplet signals of methylene protons of SCH/sub 2/ groups at 2.4-3.3 ppm (JPH 10-12 Hz, JHH 7-8 Hz) and OCH/sub 2/ groups in the region 3.6-4.4 ppm (JPH 7-10 Hz, JHH 6-7 Hz). The /sup 31/P-//sup 1/H/ NMR spectra contain singlets in the region 52-58 ppm.

• Research Organization: A. N. Nesmeyanov Institute of Organometallic Compounds, Moscow (USSR)
• OSTI ID: 5099538
• Journal Information: J. Gen. Chem. USSR (Engl. Transl.); (United States), Journal Name: J. Gen. Chem. USSR (Engl. Transl.); (United States) Vol. 57:4; ISSN JGCHA
• Country of Publication: United States
• Language: English

Related Subjects

37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
400201* -- Chemical & Physicochemical Properties
640302 -- Atomic
Molecular & Chemical Physics-- Atomic & Molecular Properties & Theory
74 ATOMIC AND MOLECULAR PHYSICS
CHEMICAL SHIFT
CHLORINATED ALIPHATIC HYDROCARBONS
CHLOROFORM
COUPLING
COUPLING CONSTANTS
DEUTERIUM COMPOUNDS
DOUBLE RESONANCE METHODS
ESTERS
HALOGENATED ALIPHATIC HYDROCARBONS
HEAVY WATER
HYDROGEN 1
HYDROGEN COMPOUNDS
HYDROGEN ISOTOPES
INFRARED SPECTRA
INTERMEDIATE COUPLING
ISOTOPES
J-J COUPLING
LIGHT NUCLEI
NMR SPECTRA
NUCLEI
ODD-EVEN NUCLEI
ORGANIC CHLORINE COMPOUNDS
ORGANIC COMPOUNDS
ORGANIC HALOGEN COMPOUNDS
ORGANIC PHOSPHORUS COMPOUNDS
ORGANIC SULFUR COMPOUNDS
OXYGEN COMPOUNDS
PHOSPHONIC ACID ESTERS
PHOSPHORUS 31
PHOSPHORUS ISOTOPES
SPECTRA
STABLE ISOTOPES
SYNTHESIS
WATER