Opening of the cyclopropane ring in. cap alpha. -bromocyclopropyl ketones by the action of triphenylphosphine
The reaction of a series of ..cap alpha..-bromocylopropyl ketones substituted in the three-membered ring with triphenylphosphine in alcohols in the presence of catalytic amounts of hydrochloric acid leads to the formation of the products from opening of the cyclopropane ring. Under analogous conditions 1-benzoyl-1-bromocyclopropane undergoes reductive dehalogenation. In boiling methanol 7-exo-benzoylbicyclo(4.1.0)heptane is converted into trans-1-bromo-2-benzoyl-methylcyclohexane by the action of a mixture of triphenylphosphine and 1-benzoyl-1-bromocyclopropane and also by a mixture of triphenylphosphine and carbon tetrabromide. The PMR spectra of solutions of the substances in carbon tetrachloride were obtained on a Tesla BS-467A instrument at 60 MHz and in deuterochloroform on a Bruker-360 instrument at 360 MHz with HMDS as internal standard. The IR spectra of solutions of the substances in carbon tetrachloride were recorded on a Specord IR-75 spectrophotometer.
- Research Organization:
- V. I. Lenin Belorussian State Univ., Minsk (USSR)
- OSTI ID:
- 6974798
- Journal Information:
- J. Org. Chem. USSR (Engl. Transl.); (United States), Journal Name: J. Org. Chem. USSR (Engl. Transl.); (United States) Vol. 23:5; ISSN JOCYA
- 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
ALCOHOLS
ALKANES
BROMINATED ALIPHATIC HYDROCARBONS
CARBON TETRACHLORIDE
CHEMICAL REACTIONS
CHEMICAL SHIFT
CHLORINATED ALIPHATIC HYDROCARBONS
CHLOROFORM
COUPLING
COUPLING CONSTANTS
CYCLOALKANES
DEHALOGENATION
DEUTERIUM COMPOUNDS
ENERGY
ESTERS
HALOGENATED ALIPHATIC HYDROCARBONS
HYDROCARBONS
HYDROGEN COMPOUNDS
HYDROXY COMPOUNDS
INFRARED SPECTRA
INTERMEDIATE COUPLING
ISOMERIZATION
J-J COUPLING
KETONES
METHANOL
MOLECULAR STRUCTURE
NMR SPECTRA
ORGANIC BROMINE COMPOUNDS
ORGANIC CHLORINE COMPOUNDS
ORGANIC COMPOUNDS
ORGANIC HALOGEN COMPOUNDS
ORGANIC PHOSPHORUS COMPOUNDS
PHOSPHINIC ACID ESTERS
SPECTRA