Triphenyldibromophosphorane has been found to effect the cleavage of dialkyl and phenyl ethyl ethers under essentially neutral conditions. Primary and secondary alkyl groups gave good yields of alkyl bromides with benzonitrile or chlorobenzene as the solvent. Cleavage of alkyl fert-butyl ethers in DMF solvent converted the iert-butyl group primarily to isobutene. No rearrangements were observed. The phenyl group was first obtained as part of a phosphonium bromide salt which was converted to bromobenzene at higher (>230°) temperartures. Vinyl and ß-chloroalkyl ethers were much less reactive. Two epoxides, a ketal, and three thioethers were treated with inconsistent results.The common methods for the cleavage of nonactivated ethers have employed strong acids. Milder conditions using boron trihalides (or diborane or sodium borohydride plus iodine) have been extended re-cently1 23
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