Reactions of polyhalogeno functional compounds with metals and electrophilic reagents. IV. Reaction of trichloroethylidene derivatives of malonic and cyanoacetic esters with zinc and acid chlorides

Journal Article · Sat Oct 10 04:00:00 EDT 1987 · J. Org. Chem. USSR (Engl. Transl.); (United States)

OSTI ID:7076387

Shchepin, V V; Rodygin, A S; Kulesh, I A; Lapkin, I I

In diethyl ether and ethyl acetate 2-(2,2,2-trichloroethylidene)malonic and 2-(2,2,2-trichloroethylidene)cyanoacetic esters react with zinc to form intermediate organozinc compounds. The hydrolysis of the latter lead to 2-(2,2-dichlorovinyl)malonic and 2-(2,2-dichloroethylidene)cyanoacetic esters. Acylation with acid chlorides leads to 2-(2,2-dichlorovinyl)-2-acylmalonic and 2-(2,2-dichlorovinyl)-2-acylcyanoacetic esters. The PMR spectra were recorded on a Tesla BS-487 instrument at 80 MHz in carbon tetrachloride with HMDS (+0.05 ppm) as internal standard. The IR spectra were recorded on a UR-20 spectrophotometer for the individual compounds. The /sup 35/Cl NQR spectrum was obtained on a pulse NQR spectrometer at 77/sup 0/K.

• Research Organization: A. M. Gor'kii Perm State Univ. (USSR)
• OSTI ID: 7076387
• 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

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
ACETIC ACID ESTERS
ACYLATION
CARBOXYLIC ACID ESTERS
CARBOXYLIC ACIDS
CATALYSIS
CATALYTIC EFFECTS
CHEMICAL REACTIONS
CHEMICAL SHIFT
CHLORINE 35
CHLORINE ISOTOPES
COMPLEXES
COUPLING
COUPLING CONSTANTS
DICARBOXYLIC ACIDS
ELEMENTS
ESTERS
HETEROGENEOUS CATALYSIS
HYDROCHLORIC ACID
HYDROGEN COMPOUNDS
INORGANIC ACIDS
INTERMEDIATE COUPLING
ISOMERIZATION
ISOTOPES
J-J COUPLING
LIGHT NUCLEI
MALONIC ACID
METALS
NMR SPECTRA
NUCLEAR QUADRUPOLE RESONANCE
NUCLEI
ODD-EVEN NUCLEI
ORGANIC ACIDS
ORGANIC CHLORINE COMPOUNDS
ORGANIC COMPOUNDS
ORGANIC HALOGEN COMPOUNDS
ORGANOMETALLIC COMPOUNDS
RESONANCE
SPECTRA
STABLE ISOTOPES
STRUCTURAL CHEMICAL ANALYSIS
ZINC
ZINC COMPLEXES