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Products derived from oxidations of 3,4-dimethyl-1-phenylphosphole-1-oxide: A 3-phenyl-5,6-dimethyl-2,3-oxaphosphabicyclo[2.2.2]octene-3-oxide derivative as a precursor of phenyl metaphosphonic anhydride

✍ Scribed by Louis D. Quin; Xiao-Ping Wu

Publisher: John Wiley and Sons
Year: 1991
Tongue: English
Weight: 704 KB
Volume: 2
Category: Article
ISSN: 1042-7163
DOI: 10.1002/hc.520020303

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✦ Synopsis

Oxidation of' 3,4-dimethyl-l-phenylphosphole with peracids or peroxides gives a relatively stable P-oxide, which can be used in Diels-Alder reactions to give derivatives with the 7-phosphanorbornene framework. Oxygen insertion into a C-P bond of this framework occurs smoothly with m-chloroperbenzoic acid (MCPBA) providing derivatives of the 2,3-oxaphosphabicyclo[2.2.2]octene ring system. The phosphole can be converted to this system in a one-pot synthesis by reaction with excess MCPBA in the presence of Nphenylmaleimide as dienophile. The phosphob oxide undergoes mono-epoxidation with MCPBA. Thermal or photochemical fragmentation of the 2,3-oxaphosphabicyclo[2.2.2]ocetene is a useful source of the 3coordinute species Ph-P02, a meta-anhydride of phenylphosphonic acid. This species was trapped successfully with a variety of alcohols.

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