CCL: Dihydroxyl compound

 Sent to CCL by: Ramon Crehuet [rcsqtc{=}iiqab.csic.es]
 Kevin,
Two hydroxyl groups on the same carbon can exist, and indeed for formaldehyde, for example, this is the major form. It is true that these hydrates or geminal diols are less stable with ketones (secondary carbons) but when substituents attract electrons, they can become also the stable form as in CF3-CO-CF3. In any case, there is always an equilibrium. This is also related to the stability of hemi-acetals. You can find more examples and the reaction mechanism in an advanced organic chemistry textbook, such as "Organic chemistry", Carey, McGraw-Hill. 
 Regards,
 Ramon
 kevin abbot kevanabbot**yahoo.com wrote:
 
 Sent to CCL by: kevin abbot [kevanabbot::yahoo.com]
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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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