Synthesis and equilibrium of stereoisomers of 5-phenyl-2-ethoxy-1,3,5-dioxaphosphorinane

Journal Article · Wed Aug 20 04:00:00 EDT 1986 · Bull. Acad. Sci. USSR, Div. Chem. Sci. (Engl. Transl.); (United States)

DOI:https://doi.org/10.1007/BF00952931· OSTI ID:6226328

Arbuzov, B A; Erastov, O A; Ionkin, A S

Bis(hydroxymethyl)phenylphosphine has two nucleophilic centers: the P and O atoms. Two types of substitution products may correspond to this. The reaction with CH/sub 3/CH(OEt)/sub 2/ and PhCH(OEt)/sub 2/ proceeded at the boiling or without heating with BF/sub 3/ etherate and gave the products of substitution at the P atom. The signals of bis(..cap alpha..-ethoxyethyl)- and bis(ethoxybenzyl)phenylphospines (-12 and -8.18 ppm) were present in the /sup 31/P NMR spectra of the reaction mixtures; this was based on the comparison with the spectra of bis(..cap alpha..-hydroxyethyl)- and bis(hydroxybenzyl)phenylphospines. Reaction with orthoformic ester gave the product of substitution at the O atom. The structure of the compound obtained was established by the methods of IR spectroscopy, /sup 1/H and /sup 31/P NMR spectroscopy, and mass spectrometry. The reaction of bis(hydroxymethyl)phenylphosphine with orthoformic ester gave 5-phenyl-2-ethoxy-1,3,5-dioxaphosphorinane, representing a mixture of two stereoisomers. The preferred conformations of these differ in the orientation of the phenyl residue on the phosphorus atom. The stereoisomer with the equatorial orientation of the phenyl radical predominates in the equilibrium.

• Research Organization: A.E. Arbuzov Institute of Organic and Physical Chemistry, Kazan, USSR
• OSTI ID: 6226328
• Journal Information: Bull. Acad. Sci. USSR, Div. Chem. Sci. (Engl. Transl.); (United States), Journal Name: Bull. Acad. Sci. USSR, Div. Chem. Sci. (Engl. Transl.); (United States) Vol. 35:2; ISSN BACCA
• Country of Publication: United States
• Language: Russian

Related Subjects

37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
400201* -- Chemical & Physicochemical Properties
BORON COMPOUNDS
BORON FLUORIDES
CARBOXYLIC ACID ESTERS
CARBOXYLIC ACIDS
CATALYTIC EFFECTS
CHEMICAL REACTIONS
CHEMICAL SHIFT
COUPLING
ELECTRON SPIN RESONANCE
ELECTRONIC STRUCTURE
EQUILIBRIUM
ESTERS
FLUORIDES
FLUORINE COMPOUNDS
FORMIC ACID
HALIDES
HALOGEN COMPOUNDS
HETEROCYCLIC COMPOUNDS
HYDROGEN 1
HYDROGEN ISOTOPES
INFRARED SPECTRA
INTERMEDIATE COUPLING
ISOMERIZATION
ISOMERS
ISOTOPES
J-J COUPLING
LIGHT NUCLEI
MAGNETIC RESONANCE
MONOCARBOXYLIC ACIDS
NMR SPECTRA
NUCLEI
ODD-EVEN NUCLEI
ORGANIC ACIDS
ORGANIC COMPOUNDS
ORGANIC PHOSPHORUS COMPOUNDS
PHOSPHINES
PHOSPHORUS 31
PHOSPHORUS COMPOUNDS
PHOSPHORUS ISOTOPES
RESONANCE
SPECTRA
STABLE ISOTOPES
STRUCTURAL CHEMICAL ANALYSIS
SYNTHESIS