M. Ramanathan, Duen‐Ren Hou
Nov 24, 2010
Citations
0
Influential Citations
13
Citations
Journal
Tetrahedron Letters
Abstract
Abstract Triphenylphosphine hydrobromide was found to cleave the benzyl ethers derived from 1°, 2° 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° 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 ·HBr offers a new and effective method for the deprotection of benzyl ethers.