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ChemInform Abstract: A Mild and Efficient Method for Converting Alcohols and Tetrahydropyranyl Ethers to Bromides with Inversion of Configuration.

✍ Scribed by A. TANAKA; T. ORITANI

No coin nor oath required. For personal study only.

✦ Synopsis

A Mild and Efficient Method for Converting Alcohols and Tetrahydropyranyl Ethers to Bromides with Inversion of Configuration.

Adding 2,4,4,5-cyclohexadienone to triphenylphosphine generates a bromotriphenylphosphonium salt which is a powerful brominating reagent for the conversion of alcohols or tetrahydropyranyl ethers to the corresponding bromides. The SN2 process results with inversion of configuration as shown for the chiral substrates (V) and (VII). -(TANAKA, A.

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