Arbuzov reaction of. cap alpha. -carbonyl phosphonites
The authors have previously found an unusual course of the Arbuzov reaction of (dialkoxymethyl)-phosphonites, resulting in the breakage of the phosphorus-carbon bond with the retention of a 3-coordinate phosphorus atom. In the present work the authors studied the Arbuzov reaction of ..cap alpha..-carbonyl phosphonites, which are structural analogs of (dialkoxymethyl)phosphonites. The ..cap alpha..-carbonyl phosphonites, with an electron-acceptor group on the phosphorus atom, react with methyl iodide only at the boil in acetonitrile by the classical Arbuzov scheme with the formation of the ..cap alpha..-carbonyl phosphinates. An unusual course of the Arbuzov reaction is realized with the breakage of the phosphorus-carbon bond at the quasiphosphonium state and the subsequent reaction of the phosphonite formed with excess of methyl chloroformate. The IR spectra were determined on a IKS-22 spectrometer (NaCl), the PMR spectra on a Tesla BS-467 spectrometer (standard TMS), and the /sup 13/C and /sup 31/P NMR spectra on a JEOL FX-100 spectrometer (standards TMS (/sup 13/C) and 85% solution of H/sub 3/PO/sub 4/ in D/sub 2/O).
- Research Organization:
- M. V. Lomonosov Moscow State Univ. (USSR)
- OSTI ID:
- 6961942
- Journal Information:
- J. Gen. Chem. USSR (Engl. Transl.); (United States), Journal Name: J. Gen. Chem. USSR (Engl. Transl.); (United States) Vol. 57:6; ISSN JGCHA
- Country of Publication:
- United States
- Language:
- English
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Related Subjects
400201* -- Chemical & Physicochemical Properties
640302 -- Atomic
Molecular & Chemical Physics-- Atomic & Molecular Properties & Theory
74 ATOMIC AND MOLECULAR PHYSICS
ACTIVATION ENERGY
BINDING ENERGY
CARBON 13
CARBON ISOTOPES
CARBOXYLIC ACID SALTS
CHEMICAL BONDS
CHEMICAL REACTIONS
CHEMICAL SHIFT
CHLORINATED ALIPHATIC HYDROCARBONS
COUPLING
COUPLING CONSTANTS
DISSOCIATION
ENERGY
EVEN-ODD NUCLEI
FORMATES
HALOGENATED ALIPHATIC HYDROCARBONS
HEAVY WATER
HYDROGEN COMPOUNDS
INFRARED SPECTRA
INTERMEDIATE COUPLING
IODINATED ALIPHATIC HYDROCARBONS
ISOMERIZATION
ISOMERS
ISOTOPES
J-J COUPLING
LIGHT NUCLEI
METHYL IODIDE
NMR SPECTRA
NUCLEI
ODD-EVEN NUCLEI
ORGANIC CHLORINE COMPOUNDS
ORGANIC COMPOUNDS
ORGANIC HALOGEN COMPOUNDS
ORGANIC IODINE COMPOUNDS
ORGANIC PHOSPHORUS COMPOUNDS
OXYGEN COMPOUNDS
PHOSPHORUS 31
PHOSPHORUS ISOTOPES
SPECTRA
STABLE ISOTOPES
STEREOCHEMISTRY
WATER