New example of ring-chain tautomerism

Journal Article · Sun Sep 20 04:00:00 UTC 1987 · J. Org. Chem. USSR (Engl. Transl.); (United States)

OSTI ID:7199866

Donskaya, N A; Bessmertnykh, A G; Shabarov, Yu S

Earlier the authors found that the reaction of sterically screened dichlorocyclobutanones with 20% aqueous potassium hydroxide solution provides a general method for the production of 5-hydroxydihydrofuran-2-ones, which can be regarded as the cyclic forms of lambda-aldehydo acids. In the present work the authors synthesized 5-hydroxy-6-oxaspiro(3,4)octan-7-one and demonstrated the possibility of ring-chain tautomerism in this compound. 5,5-Dichloro-spiro(3.3)heptan-6-one was obtained with a 45% yield from methylenecyclobutane and dichloroketone. The IR spectrum contained absorption bands for the carbonyl groups at 1780 and 1720 cm/sup -1/ and also broad absorption bands for the hydroxyl groups in the regions of 2400-2800 and 3200-3600 cm/sup -1/. The /sup 1/H NMR spectrum contains signals for six protons of the methylene groups in the cyclobutane fragment in the range of 1.6-2.7 ppm and a signal at 2.8 ppm.

• Research Organization: M. V. Lomonosov Moscow State Univ. (USSR)
• OSTI ID: 7199866
• Journal Information: J. Org. Chem. USSR (Engl. Transl.); (United States), Journal Name: J. Org. Chem. USSR (Engl. Transl.); (United States) Vol. 23:4; 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
ACETONE
ALCOHOLS
ALKALI METAL COMPOUNDS
ALKANES
CARBON 13
CARBON ISOTOPES
CHEMICAL REACTIONS
CHEMICAL SHIFT
CHLORINATED ALIPHATIC HYDROCARBONS
CHLOROFORM
COUPLING
COUPLING CONSTANTS
CYCLOALKANES
DEUTERATION
DEUTERIUM COMPOUNDS
EVEN-ODD NUCLEI
FURANS
HALOGENATED ALIPHATIC HYDROCARBONS
HETEROCYCLIC COMPOUNDS
HYDROCARBONS
HYDROGEN 1
HYDROGEN COMPOUNDS
HYDROGEN ISOTOPES
HYDROXIDES
HYDROXY COMPOUNDS
INTERMEDIATE COUPLING
ISOMERIZATION
ISOMERS
ISOTOPES
J-J COUPLING
KETONES
LIGHT NUCLEI
METHANOL
METHYLENE CHLORIDE
MOLECULAR STRUCTURE
NMR SPECTRA
NUCLEI
ODD-EVEN NUCLEI
ORGANIC CHLORINE COMPOUNDS
ORGANIC COMPOUNDS
ORGANIC HALOGEN COMPOUNDS
ORGANIC OXYGEN COMPOUNDS
OXYGEN COMPOUNDS
POTASSIUM COMPOUNDS
POTASSIUM HYDROXIDES
SPECTRA
STABLE ISOTOPES
STRUCTURAL CHEMICAL ANALYSIS