Synthesis of (diethoxyphosphoryl) acetonitrile oxide and its cycloaddition to olefins. Synthetic applications to 3,5-disubstituted 2-isoxazolines

doi:10.1246/BCSJ.60.2463

Paper

Synthesis of (diethoxyphosphoryl) acetonitrile oxide and its cycloaddition to olefins. Synthetic applications to 3,5-disubstituted 2-isoxazolines

Published Jul 1, 1987 · O. Tsuge, S. Kanemasa, H. Suga

Bulletin of the Chemical Society of Japan

Q2 SJR score

31

Citations

0

Influential Citations

Full textSemantic Scholar

Abstract

(Diethoxyphosphoryl)acetonitrile oxide undergoes regioselective cycloaddition to olefins leading to 3-[(diethoxyphosphoryl)methyl]-2-isoxazolines or -isoxazole. The phosphorus-stabilized carbanions generated by deprotonation of the cycloadducts can be utilized for the condensation with carbonyl compounds, alkylation, and oxidation with oxygen to provide 3,5-disubstituted 2-isoxazolines as useful synthetic building blocks. Raney nickel hydrogenolysis of 3-[(diethoxyphosphoryl)methyl]-2-isoxazolines gives β-hydroxy-β′-phosphoryl ketones bearing a variety of functional groups, which can be further converted into α,β-unsaturated β′-phosphoryl ketones.

Study Snapshot

(Diethoxyphosphoryl)acetonitrile oxide can be synthesized to produce 3,5-disubstituted 2-isoxazolines, useful synthetic building blocks for various functional groups.

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

Synthesis of (diethoxyphosphoryl) acetonitrile oxide and its cycloaddition to olefins. Synthetic applications to 3,5-disubstituted 2-isoxazolines

References

Citations