CCL: Dihydroxyl compound

 Sent to CCL by: "Phil Hultin" [hultin(-)cc.umanitoba.ca]
 Kevin Abbott asked about the stability of a geminal diol.
 Gem-diols (also known as carbonyl hydrates) are in general NOT
 thermodynamically stable.  The major exceptions are the hydrates of
 aldehydes bearing highly electronegative substituents on the alpha position.
 The most famous of these is chloral hydrate (a powerful sedative), which is
 1,1-dihydroxy-2,2,2-trichloroethane.  This is quite stable.  Similarly,
 bis(perfluoroalkyl)ketones form very stable hydrates.
 For most aliphatic and aryl ketones or aldehydes, the hydrate form is
 thermodynamically disfavoured relative to the carbonyl plus H2O and exists
 only to a very small extent at equilibrium in the presence of water.
 Dr. Philip G. Hultin
 Professor of Chemistry,
 University of Manitoba
 Winnipeg, MB
 R3T 2N2
 hultin:+:cc.umanitoba.ca
 http://umanitoba.ca/chemistry/people/hultin
 -----Original Message-----
 > From: owner-chemistry:+:ccl.net [mailto:owner-chemistry:+:ccl.net]
 Sent: May 10, 2006 8:54 AM
 To: Hultin, Philip G.
 Subject: CCL: Dihydroxyl compound
 Sent to CCL by: kevin abbot [kevanabbot::yahoo.com]
 --0-512180785-1147267732=:41797
 Content-Type: text/plain; charset=iso-8859-1
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 Hi CCLers,
   I am working on a compound which has two hydroxyl groups on the same
 secondary carbon atom (not primary),
   might someone inform me about the stability of a dihydroxyl compound and
 its synthetic reliability (I mean is a compound like this stable?).
   Some references are appreciated as I have found only a few articles on
 this kind of compound.
   Best Regards
   Kevin
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 <div class=MsoNormal style="MARGIN: 0cm 0cm 0pt"><SPAN
 lang=EN-GB
 style="mso-ansi-language: EN-GB"><FONT size=3><FONT
 face="Times New
 Roman">Hi CCLers,<?xml:namespace prefix = o ns =
 "urn:schemas-microsoft-com:office:office"
 /><o:p></o:p></FONT></FONT></SPAN></div>
 <div class=MsoNormal
 style="MARGIN: 0cm 0cm 0pt"><SPAN lang=EN-GB
 style="mso-ansi-language:
 EN-GB"><FONT size=3><FONT face="Times New
 Roman">I&nbsp;am
 working&nbsp;on&nbsp;a compound which has two hydroxyl groups on the
 same
 secondary carbon atom (not
 primary),<o:p></o:p></FONT></FONT></SPAN></div>
 <div class=MsoNormal style="MARGIN: 0cm 0cm 0pt"><SPAN
 lang=EN-GB
 style="mso-ansi-language: EN-GB"><FONT size=3><FONT
 face="Times New
 Roman">might someone inform me about the stability of a dihydroxyl
 compound
 and its synthetic reliability (I mean is a compound like this
 stable?).<o:p></o:p></FONT></FONT></SPAN></div>
 <div class=MsoNormal
 style="MARGIN: 0cm 0cm 0pt"><SPAN lang=EN-GB
 style="mso-ansi-language:
  EN-GB"><FONT size=3><FONT face="Times New
 Roman">Some references are
 appreciated as I have found only a few articles on this kind of
 compound.<o:p></o:p></FONT></FONT></SPAN></div>
 <div class=MsoNormal
 style="MARGIN: 0cm 0cm 0pt"><SPAN lang=EN-GB
 style="mso-ansi-language:
 EN-GB"><o:p><FONT face="Times New Roman"
 size=3>&nbsp;</FONT></o:p></SPAN></div>  <div
 class=MsoNormal style="MARGIN:
 0cm 0cm 0pt"><SPAN lang=EN-GB style="mso-ansi-language:
 EN-GB"><FONT
 size=3><FONT face="Times New Roman">Best
 Regards<o:p></o:p></FONT></FONT></SPAN></div>
 <div class=MsoNormal
 style="MARGIN: 0cm 0cm 0pt"><SPAN lang=EN-GB
 style="mso-ansi-language:
 EN-GB"><o:p><FONT face="Times New Roman"
 size=3>&nbsp;</FONT></o:p></SPAN></div>  <div
 class=MsoNormal style="MARGIN:
 0cm 0cm 0pt"><SPAN lang=EN-GB style="mso-ansi-language:
 EN-GB"><FONT
 size=3><FONT face="Times New
 Roman">Kevin<o:p></o:p></FONT></FONT></SPAN></div>
 <div>&nbsp;</div><p>
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