Hypervalent (tert-Butylperoxy) iodanes generate iodine-centered radicals at room temperature in solution: oxidation and deprotection of benzyl and allyl ethers, and …

M Ochiai, T Ito, H Takahashi, A Nakanishi…

Index: Ochiai, Masahito; Ito, Takao; Takahashi, Hideo; Nakanishi, Akinobu; Toyonari, Mika; Sueda, Takuya; Goto, Satoru; Shiro, Motoo Journal of the American Chemical Society, 1996 , vol. 118, # 33 p. 7716 - 7730

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Citation Number: 105

Abstract

1-(tert-Butylperoxy)-1, 2-benziodoxol-3 (1 H)-one (1a) oxidizes benzyl and allyl ethers to the esters at room temperature in benzene or cyclohexane in the presence of alkali metal carbonates. Since this reaction is compatible with other protecting groups such as MOM, THP, and TBDMS ethers, and acetoxy groups, and because esters are readily hydrolyzed under basic conditions, this new method provides a convenient and effective alternative to ...

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