Selective oxidation of acetylenic 1, 4-diols with dioxiranes in comparison with the methyltrioxorhenium–hydrogen peroxide oxidant

L D'Accolti, M Fiorentino, C Fusco, P Crupi, R Curci

Index: D'Accolti, Lucia; Fiorentino, Michele; Fusco, Caterina; Crupi, Pasquale; Curci, Ruggero Tetrahedron Letters, 2004 , vol. 45, # 46 p. 8575 - 8578

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Citation Number: 5

Abstract

Dimethyldioxirane () and its trifluoro analog () were employed to achieve selectively the direct transformation of hex-3-yne-2, 5-diol and 1, 4-diphenyl-but-2yne-1, 4-diol (two representative acetylenic 1, 4-diols) into the corresponding carbonyls, leaving the carbon– carbon triple bond moiety untouched. The results are compared with those recorded in the analogous oxidation using the methyltrioxorhenium (MTO)/85% H2O2 homogeneous ...