Nitriles of retinoic acids
The authors propose a single-stage synthesis for the nitrile of retinoic acid involving reaction of the all-trans-retinal with ammonium molybdate in the presence of ammonium hydroxide and hydrogen peroxide under the conditions of phase-transfer catalysis. As the authors established, this transformation is distinguished by high selectivity and is not accompanied by epoxidation or isomerization of the double bonds. In addition, the reaction evidently has general significance in the series of retinoids, and this the authors demonstrated for the case of the production of the nitriles of 3,4-didehydro-, 5,6-epoxy-5,6-dihydro-, and 4-ketoretinoic acids. The /sup 1/H NMR spectra were recorded in deuterochloroform on a Bruker WM-250 spectrometer.
- Research Organization:
- M. V. Lomonosov Moscow Institute of Fine Chemical Technology (USSR)
- OSTI ID:
- 6974865
- 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
AMMONIUM COMPOUNDS
AMMONIUM HALIDES
AMMONIUM HYDROXIDES
ANTINEOPLASTIC DRUGS
CARBOXYLIC ACID ESTERS
CATALYSIS
CATALYTIC EFFECTS
CHEMICAL REACTION YIELD
CHEMICAL SHIFT
CHLORINATED ALIPHATIC HYDROCARBONS
CHLOROFORM
COUPLING
COUPLING CONSTANTS
DEUTERIUM COMPOUNDS
DRUGS
ESTERS
HALIDES
HALOGEN COMPOUNDS
HALOGENATED ALIPHATIC HYDROCARBONS
HETEROGENEOUS CATALYSIS
HYDROGEN 1
HYDROGEN COMPOUNDS
HYDROGEN ISOTOPES
HYDROGEN PEROXIDE
HYDROXIDES
INFRARED SPECTRA
INTERMEDIATE COUPLING
IODIDES
IODINE COMPOUNDS
ISOTOPES
J-J COUPLING
LIGHT NUCLEI
MOLYBDATES
MOLYBDENUM COMPOUNDS
NITRILES
NMR SPECTRA
NUCLEI
ODD-EVEN NUCLEI
ORGANIC CHLORINE COMPOUNDS
ORGANIC COMPOUNDS
ORGANIC HALOGEN COMPOUNDS
ORGANIC NITROGEN COMPOUNDS
OXYGEN COMPOUNDS
PEROXIDES
REFRACTORY METAL COMPOUNDS
RETINOIC ACID
SPECTRA
STABLE ISOTOPES
SYNTHESIS
TRANSITION ELEMENT COMPOUNDS
YIELDS