ORGLIST: Oxidative cleavage of alkenes

Date view Thread view Subject view Author view Attachment view

From: Paul Handley (p.handley$##$chemistry.uq.edu.au)
Date: Sun Aug 08 1999 - 04:43:35 EDT

>Is it true that under certain situation\condition that C=C can be cleave by
>hot acidified dichromate?
>Why is the use of permanganate not advisable?

Hot acid Cr(VI) will probably cleave *anything* given enough time, turning
your molecule into a mixture of CO2 and H2O. Permanganate I think would be
milder, but you would still get the same problems with overoxidation in all
but the simplest alkenes.
  Perhaps you should try the Lemieux-von Rudloff reagent, HIO4 containing a
trace of MnO4-, see Can.J.Chem. 1955, 33, 1701
theres probably others as well
Paul
__________________

ORGLIST - Organic Chemistry Mailing List
Website and Archive: http://www.orglist.net/
List coordinator: Joao Aires de Sousa (jas$##$mail.fct.unl.pt)

Date view Thread view Subject view Author view Attachment view

This archive was generated by hypermail 2.1.4 : Fri Sep 19 2003 - 12:15:04 EDT