Triphenyldibromophosphorane

Dialkyl and alkyl aryl ethers can be cleaved with iodotrimethylsilane ROR -bMe3SiI — Rl-bMe3SiOR. A more convenient and less exjjensive alternative, which gives the same products, is a mixture of chlorotrimethylsilane and Nal. Alkyl aryl ethers can also be cleaved with Lil to give alkyl iodides and salts of phenols in a reaction similar to 10-73. Triphenyldibromophosphorane (Ph3PBr2) cleaves dialkyl ethers to give 2mol of alkyl bromide. ... 

In principle, a new synthetic route resulted from the treatment of lithium benzoylpentacarbonyltungstate with triphenyldibromophosphorane... 

Unfortunately, alkylation of thallium(i) salts of cyclic 1,3-diketones results in predominant O-alkylation. In a reaction of possibly general applicability to highly enolized ketones, triphenyldibromophosphorane effects the conversion of acetylacetone into 4-bromopent-3-en-2-one under mild conditions. The reaction of enolizable ketones with triphenylphosphine and carbon tetrachloride gives rise to variously halogenated and homologated derivatives. ... 

Triphenyldibromophosphorane efficiently cleaves ethers to alkyl bromides under essentially neutral conditions (Scheme 153) naturally, primary... 

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