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Synthesis 1995; 1995(8): 964-968
DOI: 10.1055/s-1995-4026
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Acyloxylation of 1-Methoxycyclohex-1-ene and Other Enol Ethers with Dimethyl Peroxydicarbonate

Kurt Schank* , Horst Beck, Susanne Pistorius, Thomas Rapold
  • *Fachrichtung 11.2 Organische Chemie der Universität des Saarlandes, D-66041 Saarbrücken, Germany, Fax +49(681)3034747; E-mail kschank@rzuni-sb.de
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Publication Date:
31 December 2000 (online)

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Acyloxylation of different types of enol ethers (derived from aldehydes and ketones) by dimethyl peroxydicarbonate (DPDC) results in either addition to the double bond or in a formal replacement of an allylic hydrogen by a methoxycarbonyloxy group forming vicinal oxygenated hydrocarbons. 1,3-Oxygenated products via monoacyloxylation could not be observed. The results are compared with copper(I)-catalyzed acyloxylations of 1-methoxycyclohex-1-ene (1a) by means of tert-butyl peroxycarboxylates 2a, b.

enol ether ‘acyloxylation’ dimethyl peroxydicarbonate (DPDC)

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