Oxidation of acetals, an orthoester, and ethers by dioxiranes through α-CH insertion
1992; Elsevier BV; Volume: 33; Issue: 29 Linguagem: Inglês
10.1016/s0040-4039(00)74695-8
ISSN1873-3581
AutoresRuggero Curci, Lucia D’Accolti, Michele Fiorentino, Caterina Fusco, Waldemar Adam, María Elena González‐Núñez, Rossella Mello,
Tópico(s)Chemistry and Chemical Engineering
ResumoDimethyldioxirane (1a) and methyl(trifluoromethyl)dioxirane (1b) efficiently afford cleavage of acetals and of ketals to carbonyl products under mild, neutral conditions. Dialkyl ethers are cleaved to alcohols, aldehydes and/or carboxylic acids, whereas reaction of dioxiranes 1a, b with medium-ring cyclic ethers transforms the latter into lactones, via the corresponding hemiacetals, with no appreciable formation of ring-opened products. The products can be accounted for on grounds of a remarkably selective O-atom insertion by the dioxirane into C-H bonds α to the ether functionality.
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