Reaction #1176842

ord-aec982f9bed9410e82658bd88d6183e0

Reaction equation

[N-]=[N+]=[N-].[Na+]
sodium azide
O=P1(Oc2ccccc2)CCCC(CI)O1
oxaphosphorinane
O=P1(Oc2ccccc2)CCCC(CI)O1
2-phenoxy-2-oxo-6-iodomethyl-1,2-oxaphosphorinane
→
[N-]=[N+]=NCC1CCCP(=O)(Oc2ccccc2)O1
2-phenoxy-2-oxo-6-(azidomethyl)-1,2-oxaphosphorinane
Yield 96.0%

Reactants

[N-]=[N+]=[N-].[Na+]
sodium azide
O=P1(Oc2ccccc2)CCCC(CI)O1
oxaphosphorinane
O=P1(Oc2ccccc2)CCCC(CI)O1
2-phenoxy-2-oxo-6-iodomethyl-1,2-oxaphosphorinane

Reagents

CCCC[N+](CCCC)(CCCC)CCCC.[Br-]
tetrabutylammonium bromide

Solvents

CN(C)C=O.c1ccccc1
benzene DMF

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Procedure

A suspension containing two equivalents of sodium azide, one equivalent of the above-prepared iodonated oxaphosphorinane and a catalytic amount of about 0.1 equivalent of tetrabutylammonium bromide in benzene/DMF (1:1) was heated to 60-80 degrees C. for 16 hours to produce 2-phenoxy-2-oxo-6-(azidomethyl)-1,2-oxaphosphorinane in 96 percent yield as a white solid.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US05079152uspto-grants-1992_01