Triphenylphosphine hydrobromide was found to cleave the benzyl ethers derived from 1 degrees, 2 degrees alkyl, and aryl alcohols to the corresponding alcohols and benzyltriphenylphosphonium bromide in good yields. Alkene and allyl phosphonium salts were produced from the benzyl ethers with 3 degrees alkyl and allyl groups, respectively. These results indicate that the formation of the product is determined by the relative stability of the carbocationic intermediate. The anhydrous, stoichiometric amount of PPh(3)center dot HBr offers a new and effective method for the deprotection of benzyl ethers. (C) 2010 Elsevier Ltd. All rights reserved.
