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), Vol. 57:6; Other Information: Translated from Zh. Obshch. Khim.; 57: No. 6, 1409-1410(Jun 1987)
- Country of Publication:
- United States
- Language:
- English
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ORGANIC
PHYSICAL AND ANALYTICAL CHEMISTRY
74 ATOMIC AND MOLECULAR PHYSICS
CHLORINATED ALIPHATIC HYDROCARBONS
ACTIVATION ENERGY
FORMATES
METHYL IODIDE
ORGANIC PHOSPHORUS COMPOUNDS
DISSOCIATION
ISOMERIZATION
NMR SPECTRA
BINDING ENERGY
CARBON 13
CHEMICAL BONDS
CHEMICAL SHIFT
COUPLING CONSTANTS
HEAVY WATER
INFRARED SPECTRA
ISOMERS
J-J COUPLING
PHOSPHORUS 31
STEREOCHEMISTRY
CARBON ISOTOPES
CARBOXYLIC ACID SALTS
CHEMICAL REACTIONS
COUPLING
ENERGY
EVEN-ODD NUCLEI
HALOGENATED ALIPHATIC HYDROCARBONS
HYDROGEN COMPOUNDS
INTERMEDIATE COUPLING
IODINATED ALIPHATIC HYDROCARBONS
ISOTOPES
LIGHT NUCLEI
NUCLEI
ODD-EVEN NUCLEI
ORGANIC CHLORINE COMPOUNDS
ORGANIC COMPOUNDS
ORGANIC HALOGEN COMPOUNDS
ORGANIC IODINE COMPOUNDS
OXYGEN COMPOUNDS
PHOSPHORUS ISOTOPES
SPECTRA
STABLE ISOTOPES
WATER
400201* - Chemical & Physicochemical Properties
640302 - Atomic
Molecular & Chemical Physics- Atomic & Molecular Properties & Theory