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Natural Science Forum / Chemistry / Organic Synthesis / April 2006Deprotection of a THP ether?
Does anybody know the specific electron-pushing mechanism for removing a THP ether or where I could possibly find it? I can't seem to find it anywhere.. Any help would be appreciated.. Thanks.. Hi there Steph, Simply protonate the OTHP, you will get,H-O+-THP, then push the electrons of the other oxigen, you will get the elimination of the ROH you have previously protected and the oxonium cation, and then beta-elimination of a H, and you?ve got it. Hope it is useful THP ethers are acetals, so you can look for the acetal hydrolysis mechanism. THP ethers are labile to mild H+ or Lewis acids. So protonate one of the O's and see what happens.... |
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