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Synthesis of azetidin-3-ones. Structure of n-tosyl-2-ethylazetidin-3-one

Journal Article · · Chem. Heterocycl. Compd. (Engl. Transl.); (United States)
DOI:https://doi.org/10.1007/BF00546731· OSTI ID:7169355
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A one-step synthesis of azetidin-3-ones by intramolecular cyclization of 1-diazo-3-arenesulfamoylalkan-2-ones was developed. The yield of cyclic product increases to 70% in the presence of an alkyl or benzyl substituent in the hydrocarbon chain of the diazoketone. The structure of N-tosyl-2-ethylazetidin-3-one was studied by x-ray diffraction analysis and it was shown that the four-membered ring has 15/sup 0/ inflection. IR spectra were recorded with a Specord 75 IR instrument in mineral oil. PMR spectra were recorded with Bruker WH-360 (360 MHz) and Jeol HL-60 (60 MHz) instruments in CDCl/sub 3/ solution, with TMS internal standard. UV spectra were obtained with a Specord UV-VIS instrument in methanol.
Research Organization:
Institute of Chemical Physics, Chernogolovka (USSR)
OSTI ID:
7169355
Journal Information:
Chem. Heterocycl. Compd. (Engl. Transl.); (United States), Journal Name: Chem. Heterocycl. Compd. (Engl. Transl.); (United States) Vol. 23:4; ISSN CHCCA
Country of Publication:
United States
Language:
English

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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
CHEMICAL REACTION YIELD
CHEMICAL REACTIONS
CHEMICAL SHIFT
CHLORINATED ALIPHATIC HYDROCARBONS
CHLOROFORM
COHERENT SCATTERING
CONFIGURATION INTERACTION
COUPLING
COUPLING CONSTANTS
DEHYDROCYCLIZATION
DEUTERIUM COMPOUNDS
DIFFRACTION
ENERGY LEVELS
EXCITED STATES
HALOGENATED ALIPHATIC HYDROCARBONS
HETEROCYCLIC COMPOUNDS
HYDROGEN COMPOUNDS
INFRARED SPECTRA
INTERMEDIATE COUPLING
ISOMERIZATION
ISOTOPE EFFECTS
J-J COUPLING
KETONES
NMR SPECTRA
ORGANIC CHLORINE COMPOUNDS
ORGANIC COMPOUNDS
ORGANIC HALOGEN COMPOUNDS
ORGANIC NITROGEN COMPOUNDS
ORGANIC SULFUR COMPOUNDS
SCATTERING
SPECTRA
SYNTHESIS
ULTRAVIOLET SPECTRA
VIBRATIONAL STATES
X-RAY DIFFRACTION
YIELDS