CCL: Dihydroxyl compound



Kevin,
 There is an equilibrium between dihydroxyl and carbonyl + water.  Unless
 there is a strong electron withdrawing group, or significant steric strain
 due to a small ring, or an enzyme transition state to stabilize it, such a
 dihydroxyl compound will not be stable and the equilibrium lies far on the
 carbonyl side.   Basic organic texts should cover this.
 Dominic
 Ps, direct mail to your address bounced.
 -----Original Message-----
 > From: owner-chemistry..ccl.net [mailto:owner-chemistry..ccl.net]
 Sent: Wednesday, May 10, 2006 8:52 AM
 To: Ryan, M Dominic
 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
 Content-Transfer-Encoding: 8bit
 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
 ---------------------------------
 New Yahoo! Messenger with Voice. Call regular phones from your PC and save
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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>
             <hr size=1>New Yahoo! Messenger with Voice. <a
 href="http://us.rd.yahoo.com/mail_us/taglines/postman5/*http://us.rd.yahoo.c
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 <p class=3DMsoNormal><font size=3D2 face=3D"Courier
 New"><span =
 style=3D'font-size:10.0pt;
 font-family:"Courier New"'>Kevin,
 <o:p></o:p></span></font></p>
 <p class=3DMsoNormal><font size=3D2 face=3D"Courier
 New"><span =
 style=3D'font-size:10.0pt;
 font-family:"Courier
 New"'><o:p>&nbsp;</o:p></span></font></p>
 <p class=3DMsoNormal><font size=3D2 face=3D"Courier
 New"><span =
 style=3D'font-size:10.0pt;
 font-family:"Courier New"'>There is an equilibrium between
 dihydroxyl =
 and
 carbonyl + water.&nbsp; Unless there is a strong electron withdrawing =
 group, or
 significant steric strain due to a small ring, or an enzyme transition =
 state to
 stabilize it, such a dihydroxyl compound will not be stable and the =
 equilibrium
 lies far on the carbonyl side.&nbsp;&nbsp; Basic organic texts should =
 cover this. <o:p></o:p></span></font></p>
 <p class=3DMsoPlainText><font size=3D2 face=3D"Courier
 New"><span =
 style=3D'font-size:
 10.0pt'><o:p>&nbsp;</o:p></span></font></p>
 <p class=3DMsoPlainText><font size=3D2 face=3D"Courier
 New"><span =
 style=3D'font-size:
 10.0pt'>Dominic<o:p></o:p></span></font></p>
 <p class=3DMsoPlainText><font size=3D2 face=3D"Courier
 New"><span =
 style=3D'font-size:
 10.0pt'><o:p>&nbsp;</o:p></span></font></p>
 <p class=3DMsoPlainText><font size=3D2 face=3D"Courier
 New"><span =
 style=3D'font-size:
 10.0pt'>Ps, direct mail to your address =
 bounced.<o:p></o:p></span></font></p>
 <p class=3DMsoPlainText><font size=3D2 face=3D"Courier
 New"><span =
 style=3D'font-size:
 10.0pt'><o:p>&nbsp;</o:p></span></font></p>
 <p class=3DMsoPlainText><font size=3D2 face=3D"Courier
 New"><span =
 style=3D'font-size:
 10.0pt'>-----Original Message-----<br>
 > From: owner-chemistry..ccl.net [mailto:owner-chemistry..ccl.net] <br>
 Sent: Wednesday, May 10, 2006 8:52 AM<br>
 To: Ryan, M Dominic <br>
 Subject: CCL: Dihydroxyl compound</span></font></p>
 <p class=3DMsoPlainText><font size=3D2 face=3D"Courier
 New"><span =
 style=3D'font-size:
 10.0pt'><o:p>&nbsp;</o:p></span></font></p>
 <p class=3DMsoPlainText><font size=3D2 face=3D"Courier
 New"><span =
 style=3D'font-size:
 10.0pt'>Sent to CCL by: kevin abbot =
 [kevanabbot::yahoo.com]<o:p></o:p></span></font></p>
 <p class=3DMsoPlainText><font size=3D2 face=3D"Courier
 New"><span =
 style=3D'font-size:
 10.0pt'>--0-512180785-1147267732=3D:41797<o:p></o:p></span></font></p>
 <p class=3DMsoPlainText><font size=3D2 face=3D"Courier
 New"><span =
 style=3D'font-size:
 10.0pt'>Content-Type: text/plain; =
 charset=3Diso-8859-1<o:p></o:p></span></font></p>
 <p class=3DMsoPlainText><font size=3D2 face=3D"Courier
 New"><span =
 style=3D'font-size:
 10.0pt'>Content-Transfer-Encoding:
 8bit<o:p></o:p></span></font></p>
 <p class=3DMsoPlainText><font size=3D2 face=3D"Courier
 New"><span =
 style=3D'font-size:
 10.0pt'><o:p>&nbsp;</o:p></span></font></p>
 <p class=3DMsoPlainText><font size=3D2 face=3D"Courier
 New"><span =
 style=3D'font-size:
 10.0pt'>Hi CCLers,<o:p></o:p></span></font></p>
 <p class=3DMsoPlainText><font size=3D2 face=3D"Courier
 New"><span =
 style=3D'font-size:
 10.0pt'>&nbsp; I am working on a compound which has two hydroxyl groups =
 on the same
 secondary carbon atom (not
 primary),<o:p></o:p></span></font></p>
 <p class=3DMsoPlainText><font size=3D2 face=3D"Courier
 New"><span =
 style=3D'font-size:
 10.0pt'>&nbsp; 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></span></font></p>
 <p class=3DMsoPlainText><font size=3D2 face=3D"Courier
 New"><span =
 style=3D'font-size:
 10.0pt'>&nbsp; Some references are appreciated as I have found only a =
 few articles
 on this kind of
 compound.<o:p></o:p></span></font></p>
 <p class=3DMsoPlainText><font size=3D2 face=3D"Courier
 New"><span =
 style=3D'font-size:
 10.0pt'>&nbsp;&nbsp;
 <o:p></o:p></span></font></p>
 <p class=3DMsoPlainText><font size=3D2 face=3D"Courier
 New"><span =
 style=3D'font-size:
 10.0pt'>&nbsp; Best
 Regards<o:p></o:p></span></font></p>
 <p class=3DMsoPlainText><font size=3D2 face=3D"Courier
 New"><span =
 style=3D'font-size:
 10.0pt'>&nbsp;&nbsp;
 <o:p></o:p></span></font></p>
 <p class=3DMsoPlainText><font size=3D2 face=3D"Courier
 New"><span =
 style=3D'font-size:
 10.0pt'>&nbsp;
 Kevin<o:p></o:p></span></font></p>
 <p class=3DMsoPlainText><font size=3D2 face=3D"Courier
 New"><span =
 style=3D'font-size:
 10.0pt'>&nbsp;&nbsp;
 <o:p></o:p></span></font></p>
 <p class=3DMsoPlainText><font size=3D2 face=3D"Courier
 New"><span =
 style=3D'font-size:
 10.0pt'><o:p>&nbsp;</o:p></span></font></p>
 <p class=3DMsoPlainText><font size=3D2 face=3D"Courier
 New"><span =
 style=3D'font-size:
 10.0pt'>&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp=
 ; <o:p></o:p></span></font></p>
 <p class=3DMsoPlainText><font size=3D2 face=3D"Courier
 New"><span =
 style=3D'font-size:
 10.0pt'>---------------------------------<o:p></o:p></span></font></p>
 <p class=3DMsoPlainText><font size=3D2 face=3D"Courier
 New"><span =
 style=3D'font-size:
 10.0pt'>New Yahoo! Messenger with Voice. Call regular phones from your =
 PC and
 save big.<o:p></o:p></span></font></p>
 <p class=3DMsoPlainText><font size=3D2 face=3D"Courier
 New"><span =
 style=3D'font-size:
 10.0pt'>--0-512180785-1147267732=3D:41797<o:p></o:p></span></font></p>
 <p class=3DMsoPlainText><font size=3D2 face=3D"Courier
 New"><span =
 style=3D'font-size:
 10.0pt'>Content-Type: text/html; =
 charset=3Diso-8859-1<o:p></o:p></span></font></p>
 <p class=3DMsoPlainText><font size=3D2 face=3D"Courier
 New"><span =
 style=3D'font-size:
 10.0pt'>Content-Transfer-Encoding:
 8bit<o:p></o:p></span></font></p>
 <p class=3DMsoPlainText><font size=3D2 face=3D"Courier
 New"><span =
 style=3D'font-size:
 10.0pt'><o:p>&nbsp;</o:p></span></font></p>
 <p class=3DMsoPlainText><font size=3D2 face=3D"Courier
 New"><span =
 style=3D'font-size:
 10.0pt'>&lt;div class=3DMsoNormal style=3D&quot;MARGIN: 0cm 0cm
 0pt&quot;&gt;&lt;SPAN lang=3DEN-GB
 style=3D&quot;mso-ansi-language:
 EN-GB&quot;&gt;&lt;FONT size=3D3&gt;&lt;FONT
 face=3D&quot;Times New
 Roman&quot;&gt;Hi CCLers,&lt;?xml:namespace prefix =3D o ns =3D =
 &quot;urn:schemas-microsoft-com:office:office&quot;
 /&gt;&lt;o:p&gt;&lt;/o:p&gt;&lt;/FONT&gt;&lt;/FONT&gt;&lt;/SPAN&gt;&lt;/d=
 iv&gt;&nbsp;
 &lt;div class=3DMsoNormal style=3D&quot;MARGIN: 0cm 0cm =
 0pt&quot;&gt;&lt;SPAN
 lang=3DEN-GB style=3D&quot;mso-ansi-language:
 EN-GB&quot;&gt;&lt;FONT
 size=3D3&gt;&lt;FONT face=3D&quot;Times New
 Roman&quot;&gt;I&amp;nbsp;am
 working&amp;nbsp;on&amp;nbsp;a compound which has two hydroxyl groups on
 =
 the
 same secondary carbon atom (not
 primary),&lt;o:p&gt;&lt;/o:p&gt;&lt;/FONT&gt;&lt;/FONT&gt;&lt;/SPAN&gt;&l=
 t;/div&gt;&nbsp;
 &lt;div class=3DMsoNormal style=3D&quot;MARGIN: 0cm 0cm =
 0pt&quot;&gt;&lt;SPAN
 lang=3DEN-GB style=3D&quot;mso-ansi-language:
 EN-GB&quot;&gt;&lt;FONT
 size=3D3&gt;&lt;FONT face=3D&quot;Times New
 Roman&quot;&gt;might someone =
 inform me
 about the stability of a dihydroxyl compound and its synthetic =
 reliability (I
 mean is a compound like this
 stable?).&lt;o:p&gt;&lt;/o:p&gt;&lt;/FONT&gt;&lt;/FONT&gt;&lt;/SPAN&gt;&l=
 t;/div&gt;&nbsp;
 &lt;div class=3DMsoNormal style=3D&quot;MARGIN: 0cm 0cm =
 0pt&quot;&gt;&lt;SPAN
 lang=3DEN-GB =
 style=3D&quot;mso-ansi-language:<o:p></o:p></span></font></p>
 <p class=3DMsoPlainText><font size=3D2 face=3D"Courier
 New"><span =
 style=3D'font-size:
 10.0pt'>&nbsp;EN-GB&quot;&gt;&lt;FONT
 size=3D3&gt;&lt;FONT =
 face=3D&quot;Times New Roman&quot;&gt;Some
 references are appreciated as I have found only a few articles on this =
 kind of
 compound.&lt;o:p&gt;&lt;/o:p&gt;&lt;/FONT&gt;&lt;/FONT&gt;&lt;/SPAN&gt;&l=
 t;/div&gt;&nbsp;
 &lt;div class=3DMsoNormal style=3D&quot;MARGIN: 0cm 0cm =
 0pt&quot;&gt;&lt;SPAN
 lang=3DEN-GB style=3D&quot;mso-ansi-language: =
 EN-GB&quot;&gt;&lt;o:p&gt;&lt;FONT
 face=3D&quot;Times New Roman&quot;
 size=3D3&gt;&amp;nbsp;&lt;/FONT&gt;&lt;/o:p&gt;&lt;/SPAN&gt;&lt;/div&gt;&=
 nbsp; &lt;div
 class=3DMsoNormal style=3D&quot;MARGIN: 0cm 0cm
 0pt&quot;&gt;&lt;SPAN =
 lang=3DEN-GB
 style=3D&quot;mso-ansi-language: EN-GB&quot;&gt;&lt;FONT =
 size=3D3&gt;&lt;FONT face=3D&quot;Times
 New Roman&quot;&gt;Best
 Regards&lt;o:p&gt;&lt;/o:p&gt;&lt;/FONT&gt;&lt;/FONT&gt;&lt;/SPAN&gt;&lt;=
 /div&gt;&nbsp;
 &lt;div class=3DMsoNormal style=3D&quot;MARGIN: 0cm 0cm =
 0pt&quot;&gt;&lt;SPAN
 lang=3DEN-GB style=3D&quot;mso-ansi-language: =
 EN-GB&quot;&gt;&lt;o:p&gt;&lt;FONT
 face=3D&quot;Times New Roman&quot;
 size=3D3&gt;&amp;nbsp;&lt;/FONT&gt;&lt;/o:p&gt;&lt;/SPAN&gt;&lt;/div&gt;&=
 nbsp; &lt;div
 class=3DMsoNormal style=3D&quot;MARGIN: 0cm 0cm
 0pt&quot;&gt;&lt;SPAN =
 lang=3DEN-GB
 style=3D&quot;mso-ansi-language: EN-GB&quot;&gt;&lt;FONT =
 size=3D3&gt;&lt;FONT
 face=3D&quot;Times New
 Roman&quot;&gt;Kevin&lt;o:p&gt;&lt;/o:p&gt;&lt;/FONT&gt;&lt;/FONT&gt;&lt;=
 /SPAN&gt;&lt;/div&gt;&nbsp;
 &lt;div&gt;&amp;nbsp;&lt;/div&gt;&lt;p&gt;<o:p></o:p></span></font></p>
 <p class=3DMsoPlainText><font size=3D2 face=3D"Courier
 New"><span =
 style=3D'font-size:
 10.0pt'>&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp=
 ; &lt;hr size=3D1&gt;New Yahoo! Messenger with Voice. &lt;a
 href=3D&quot;http://us.rd.yahoo.com/mail_us/taglines/postman5/*http://us.=
 rd.yahoo.com/evt=3D39666/*http://messenger.yahoo.com&quot;&gt;Call
 regular phones from your PC&lt;/a&gt; and save =
 big.<o:p></o:p></span></font></p>
 <p class=3DMsoPlainText><font size=3D2 face=3D"Courier
 New"><span =
 style=3D'font-size:
 10.0pt'>--0-512180785-1147267732=3D:41797--<o:p></o:p></span></font></p>
 <p class=3DMsoPlainText><font size=3D2 face=3D"Courier
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 <p class=3DMsoPlainText><font size=3D2 face=3D"Courier
 New"><span =
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 <p class=3DMsoPlainText><font size=3D2 face=3D"Courier
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 <p class=3DMsoPlainText><font size=3D2 face=3D"Courier
 New"><span =
 style=3D'font-size:
 10.0pt'>-=3D This is automatically added to each message by the mailing =
 script =3D-<o:p></o:p></span></font></p>
 <p class=3DMsoPlainText><font size=3D2 face=3D"Courier
 New"><span =
 style=3D'font-size:
 10.0pt'>To recover the email address of the author of the message, =
 please
 change<o:p></o:p></span></font></p>
 <p class=3DMsoPlainText><font size=3D2 face=3D"Courier
 New"><span =
 style=3D'font-size:
 10.0pt'>the strange characters on the top line to the .. sign. You can =
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 <p class=3DMsoPlainText><font size=3D2 face=3D"Courier
 New"><span =
 style=3D'font-size:
 10.0pt'>look up the X-Original-From: line in the mail =
 header.<o:p></o:p></span></font></p>
 <p class=3DMsoPlainText><font size=3D2 face=3D"Courier
 New"><span =
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 <p class=3DMsoPlainText><font size=3D2 face=3D"Courier
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 =<o:p></o:p></span></font><=
 /p>
 <p class=3DMsoPlainText><font size=3D2 face=3D"Courier
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 style=3D'font-size:
 10.0pt'><o:p>&nbsp;</o:p></span></font></p>
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 New"><span =
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 <p class=3DMsoPlainText><font size=3D2 face=3D"Courier
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 10.0pt'>&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;
 =<o:p></o:p></span></font><=
 /p>
 <p class=3DMsoPlainText><font size=3D2 face=3D"Courier
 New"><span =
 style=3D'font-size:
 10.0pt'><o:p>&nbsp;</o:p></span></font></p>
 <p class=3DMsoPlainText><font size=3D2 face=3D"Courier
 New"><span =
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 10.0pt'<o:p></o:p></span></font></p>
 <p class=3DMsoPlainText><font size=3D2 face=3D"Courier
 New"><span =
 style=3D'font-size:
 10.0pt'>&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;
 =<o:p></o:p></span></font></p>=
 <p class=3DMsoPlainText><font size=3D2 face=3D"Courier
 New"><span =
 style=3D'font-size:
 10.0pt'><o:p>&nbsp;</o:p></span></font></p>
 <p class=3DMsoPlainText><font size=3D2 face=3D"Courier
 New"><span =
 style=3D'font-size:
 10.0pt'>Before posting, check wait time at: =
 http://www.ccl.net<o:p></o:p></span></font></p>;
 <p class=3DMsoPlainText><font size=3D2 face=3D"Courier
 New"><span =
 style=3D'font-size:
 10.0pt'><o:p>&nbsp;</o:p></span></font></p>
 <p class=3DMsoPlainText><font size=3D2 face=3D"Courier
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 10.0pt'<o:p></o:p></span></font></p>
 <p class=3DMsoPlainText><font size=3D2 face=3D"Courier
 New"><span =
 style=3D'font-size:
 10.0pt'>Conferences: =
 http://server.ccl.net/chemistry/announcements/conferences/<o:p></o:p></sp=
 an></font></p>
 <p class=3DMsoPlainText><font size=3D2 face=3D"Courier
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 style=3D'font-size:
 10.0pt'><o:p>&nbsp;</o:p></span></font></p>
 <p class=3DMsoPlainText><font size=3D2 face=3D"Courier
 New"><span =
 style=3D'font-size:
 10.0pt'>Search Messages: http://www.ccl.net/htdig&nbsp; (login: ccl, =
 Password:
 search)<o:p></o:p></span></font></p>
 <p class=3DMsoPlainText><font size=3D2 face=3D"Courier
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 10.0pt'><o:p>&nbsp;</o:p></span></font></p>
 <p class=3DMsoPlainText><font size=3D2 face=3D"Courier
 New"><span =
 style=3D'font-size:
 10.0pt'>If your mail bounces from CCL with 5.7.1 error, =
 check:<o:p></o:p></span></font></p>
 <p class=3DMsoPlainText><font size=3D2 face=3D"Courier
 New"><span =
 style=3D'font-size:
 10.0pt'>&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;
 =<o:p></o:p></span></font></p>
 <p class=3DMsoPlainText><font size=3D2 face=3D"Courier
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 <p class=3DMsoPlainText><font size=3D2 face=3D"Courier
 New"><span =
 style=3D'font-size:
 10.0pt'>RTFI: =
 http://www.ccl.net/chemistry/aboutccl/instructions/<o:p></o:p></span></fo=
 nt></p>
 <p class=3DMsoPlainText><font size=3D2 face=3D"Courier
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 10.0pt'><o:p>&nbsp;</o:p></span></font></p>
 <p class=3DMsoPlainText><font size=3D2 face=3D"Courier
 New"><span =
 style=3D'font-size:
 10.0pt'>-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-=
 +-+-+-+<o:p></o:p></span></font></p>
 <p class=3DMsoPlainText><font size=3D2 face=3D"Courier
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 style=3D'font-size:
 10.0pt'><o:p>&nbsp;</o:p></span></font></p>
 <p class=3DMsoPlainText><font size=3D2 face=3D"Courier
 New"><span =
 style=3D'font-size:
 10.0pt'><o:p>&nbsp;</o:p></span></font></p>
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