From: Jack Kellum (jkellum$##$ucsd.edu)
Date: Thu Mar 09 2000 - 12:17:24 EST
Upon consulting Greene's book on protective groups, I see that cyclic
thioacetals (formed from aldehyde + ethane dithiol) can be cleaved with
mercury (II) perchlorate. OTOH, acyclic thioacetals (formed from aldehyde +
ethanethiol) are shown to be cleaved with a mix of mercury (II) chloride and
mercury (II) oxide. Is it reasonable to assume that the acyclic
dithioacetal will cleave with mercury (II) perchlorate? Is it six of one
and half a dozen of the other with respect to the two sets of conditions
effecting essentially the same cleavage? The reason I ask is that I have on
hand ethanethiol and mercury (II) perchlorate, but no EDT or other mercury
salts. I would think that the important thing is that mercury (II) is
present, and less important is the counterion. Any thoughts? Yeah, yeah, I
can always try the reaction on small scale and see if it works but before I
start generating mercury waste I'd like some informed opinions first.
Also, has anyone ever cleaved an acyclic dithioacetal with NBS? What might
the advantages/disadvantages be with the use of this reagent besides
avoiding the highly toxic mercury or silver salts usually employed in these
conditions?
Thanks in advance for all relevant responses.
Jack
__________________
ORGLIST - Organic Chemistry Mailing List
Website and Archive: http://www.orglist.net/
List coordinator: Joao Aires de Sousa (jas$##$mail.fct.unl.pt)
This archive was generated by hypermail 2.1.4 : Fri Sep 19 2003 - 12:15:34 EDT