Synthesis of 2-cyclobuten-1-ylphosphonates by the thermal cyclization of 1,3-butadienylphosphonates
Journal Article
·
· J. Gen. Chem. USSR (Engl. Transl.); (United States)
OSTI ID:7005393
Heating (1-alkyl(aryl)-3-tert-butyl-chloro-1,3-butadienyl)phosphonic dichlorides leads to electrocyclic thermal cyclization with the formation of (1-alkyl(aryl)-3-tert-butyl-2-chloro(methylthio)-2-cyclobuten-1-yl)phosphonic dichlorides. It was shown that the replacement of a chlorine atom by an alkylthio group in a 1,3-alkadienylphosphonic dichloride does not influence the course of the reaction, but the replacement of one of the protons of the terminal =CH/sub 2/ group of the original diene by a chlorine atom makes butadiene-cyclobutene conversion impossible under analogous conditions; the replacement of a chlorine atom in the phosphonic dichloride grouping by phenyl makes cyclization more difficult. The PMR spectra were determined on a Tesla BS-497 spectrometer (100 MHz) with the use of hexamethyldisiloxane as standard. /sup 31/P chemical shifts were determined by the /sup 31/P NMR method on a spectrometer with a working frequency of 16.2 MHz.
- OSTI ID:
- 7005393
- Journal Information:
- J. Gen. Chem. USSR (Engl. Transl.); (United States), Journal Name: J. Gen. Chem. USSR (Engl. Transl.); (United States) Vol. 57:7; ISSN JGCHA
- Country of Publication:
- United States
- Language:
- English
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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
ALKENES
BUTADIENE
BUTENES
CHEMICAL REACTIONS
CHEMICAL SHIFT
COUPLING
COUPLING CONSTANTS
CYCLOALKENES
DEHYDROCYCLIZATION
DIENES
ESTERS
HYDROCARBONS
INFRARED SPECTRA
INTERMEDIATE COUPLING
ISOMERIZATION
ISOTOPES
J-J COUPLING
LIGHT NUCLEI
MULTIPLETS
NMR SPECTRA
NUCLEI
ODD-EVEN NUCLEI
ORGANIC CHLORINE COMPOUNDS
ORGANIC COMPOUNDS
ORGANIC HALOGEN COMPOUNDS
ORGANIC PHOSPHORUS COMPOUNDS
PHOSPHONIC ACID ESTERS
PHOSPHORUS 31
PHOSPHORUS ISOTOPES
POLYENES
SPECTRA
STABLE ISOTOPES
SYNTHESIS
TEMPERATURE EFFECTS
THERMOCHEMICAL PROCESSES
400201* -- Chemical & Physicochemical Properties
640302 -- Atomic
Molecular & Chemical Physics-- Atomic & Molecular Properties & Theory
74 ATOMIC AND MOLECULAR PHYSICS
ALKENES
BUTADIENE
BUTENES
CHEMICAL REACTIONS
CHEMICAL SHIFT
COUPLING
COUPLING CONSTANTS
CYCLOALKENES
DEHYDROCYCLIZATION
DIENES
ESTERS
HYDROCARBONS
INFRARED SPECTRA
INTERMEDIATE COUPLING
ISOMERIZATION
ISOTOPES
J-J COUPLING
LIGHT NUCLEI
MULTIPLETS
NMR SPECTRA
NUCLEI
ODD-EVEN NUCLEI
ORGANIC CHLORINE COMPOUNDS
ORGANIC COMPOUNDS
ORGANIC HALOGEN COMPOUNDS
ORGANIC PHOSPHORUS COMPOUNDS
PHOSPHONIC ACID ESTERS
PHOSPHORUS 31
PHOSPHORUS ISOTOPES
POLYENES
SPECTRA
STABLE ISOTOPES
SYNTHESIS
TEMPERATURE EFFECTS
THERMOCHEMICAL PROCESSES