3-phosphorylated and -thiophosphorylated 2-thiazolidine- and 2-oxazolidine-thiones

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

OSTI ID:5023010

Vorob'eva, N N; Razvodovskaya, L V; Negrebetskii, V V; Grapov, A F; Mel'nikov, N N

We investigated the phosphorylation and thiophosphorylation of 2-thiazolidine- and 2-oxazolidine-thiones. The presence in the heterocycle of the ambident triad HN-C=S can also lead to two series of phosphorylation products formed at the nitrogen and at the sulfur atom. It was therefore of interest to determine the dependence of the site of the phosphorylation on the structures of the heterocycle and off the phosphorylating agent. The formation of the N-phosphorylation products is confirmed by the /sup 1/H NMR spectra, in which the signals of protons of the methylene group of the heteroring (C/sup 4/H/sub 2/) are split on account of interaction with the phosphorus atom (/sup 3/JPH 0.5-2.3 Hz). We observed analogous values of /sup 3/JPH constants for 2-aminothiazolines phosphorylated on the endocyclic nitrogen atom. In the /sup 13/C NMR spectra of these compounds there are also coupling constants for the interaction of the carbon atoms C/sup 4/ and C/sup 5/ of the heterocycle with the phosphorus atom. The existence of the compounds as N-phosphorylated heterocycles is evidenced also by the /sup 31/P chemical shifts.

• Research Organization: All-Union Research Institute of Chemical Means for the Protection of Plants, Moscow (USSR)
• OSTI ID: 5023010
• Journal Information: J. Gen. Chem. USSR (Engl. Transl.); (United States), Journal Name: J. Gen. Chem. USSR (Engl. Transl.); (United States) Vol. 57:4; ISSN JGCHA
• 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
AZOLES
CARBON 13
CARBON ISOTOPES
CHEMICAL REACTIONS
CHEMICAL SHIFT
COUPLING
COUPLING CONSTANTS
EVEN-ODD NUCLEI
HETEROCYCLIC COMPOUNDS
HYDROGEN 1
HYDROGEN ISOTOPES
HYPERFINE STRUCTURE
INFRARED SPECTRA
INTERMEDIATE COUPLING
ISOTOPES
J-J COUPLING
LIGHT NUCLEI
NMR SPECTRA
NUCLEI
ODD-EVEN NUCLEI
ORGANIC COMPOUNDS
ORGANIC NITROGEN COMPOUNDS
ORGANIC OXYGEN COMPOUNDS
ORGANIC PHOSPHORUS COMPOUNDS
ORGANIC SULFUR COMPOUNDS
OXAZOLES
PHOSPHORUS 31
PHOSPHORUS ISOTOPES
PHOSPHORYLATION
SPECTRA
STABLE ISOTOPES
THIAZOLES