Synthesis of bis(2-chloroethyl)amides of polyhydroxy acids
The bis(2-chloroethyl)amides of peracetylated L-arabonic, D-gluconic, and D-galactaric acids were synthesized. The acetyl protection in the obtained compounds is removed anomalously in alkaline media (ammonia, triethylamine, barium methoxide), but in acidic media (HCl) complete deacetylation occurs with the formation of the bis(2-chloroethyl)amides of the respective acids. The PMR spectra were obtained on a Tesla BS-497 spectrometer at 100 MHz in deuterochloroform with HMDS as internal standard. The chemical shifts are given with reference to TMS. The /sup 13/C NMR spectra were recorded on a Bruker WM-250 instrument at 62.89 MHz in deuterochloroform or heavy water with methanol as standard.
- Research Organization:
- Tbilisi State Univ. (USSR)
- OSTI ID:
- 6974885
- 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
Similar Records
Opening of the cyclopropane ring in. cap alpha. -bromocyclopropyl ketones by the action of triphenylphosphine
Conversion of 5-hydroxy to 5-amino and 5-alkoxypyrazolidines
Related Subjects
400201* -- Chemical & Physicochemical Properties
640302 -- Atomic
Molecular & Chemical Physics-- Atomic & Molecular Properties & Theory
74 ATOMIC AND MOLECULAR PHYSICS
ACETYLATION
ACYLATION
ALKYLATING AGENTS
AMIDES
ANTINEOPLASTIC DRUGS
CARBON 13
CARBON ISOTOPES
CARBOXYLIC ACIDS
CHEMICAL REACTIONS
CHEMICAL SHIFT
CHLORINATED ALIPHATIC HYDROCARBONS
CHLOROFORM
COUPLING
COUPLING CONSTANTS
DEUTERIUM COMPOUNDS
DRUGS
ELECTRON SPIN RESONANCE
EVEN-ODD NUCLEI
HALOGENATED ALIPHATIC HYDROCARBONS
HEAVY WATER
HYDROGEN COMPOUNDS
HYDROXY ACIDS
INFRARED SPECTRA
INTERMEDIATE COUPLING
ISOTOPES
J-J COUPLING
LIGHT NUCLEI
MAGNETIC RESONANCE
MASS SPECTRA
NMR SPECTRA
NUCLEI
ORGANIC ACIDS
ORGANIC CHLORINE COMPOUNDS
ORGANIC COMPOUNDS
ORGANIC HALOGEN COMPOUNDS
ORGANIC NITROGEN COMPOUNDS
OXYGEN COMPOUNDS
RESONANCE
SPECTRA
STABLE ISOTOPES
STRUCTURAL CHEMICAL ANALYSIS
SYNTHESIS
WATER