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<meta content="Canty, A.J." name="eprints.creators_name" />
<meta content="George, E.E." name="eprints.creators_name" />
<meta content="Lee, C.V." name="eprints.creators_name" />
<meta content="allan.canty@utas.edu.au" name="eprints.creators_id" />
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<meta content="2008-01-11 04:32:28" name="eprints.datestamp" />
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<meta content="Synthesis of Ketones and Methanols Containing
Pyridinyl and N-Methylimidazolyl Groups" name="eprints.title" />
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<meta content="N-Methylimidazolyllithium reacts with N-methylimidazole-2-carbaldehyde to form bis(N-methylimidazol-2-yl)methanol, and with the esters ethyl N-methylimidazole-2-carboxylate and ethyl pyridine-2-carboxylate to give bis(N-methylimidazol-2-yl)methanone, (mim)2CO, and (N-methylimidazol-2-yl)(pyridin-2-yl)methanone, (Py)(mim)CO, respectively. The ketones react with
N-methylimidazolyllithium to give tris(N-methylimidazol-2-yl)methanol,(mim)3COH, and bis(N-methylimidazol-
2-yl)(pyridin-2-y1)methanol(Py)(mim)2COH, respectively." name="eprints.abstract" />
<meta content="1983" name="eprints.date" />
<meta content="published" name="eprints.date_type" />
<meta content="Australian Journal of Chemistry" name="eprints.publication" />
<meta content="36" name="eprints.volume" />
<meta content="2" name="eprints.number" />
<meta content="415-418" name="eprints.pagerange" />
<meta content="10.1071/CH9830415" name="eprints.id_number" />
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<meta content="0004-9425" name="eprints.issn" />
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(1) (a) University of Tasmania. (b) University of Western Australia.
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307; Synth. React. Inorg. Met.-Org. Chem. 1977, 7, 235.
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(10) For a recent review, see: Stille, J. K. In The Chemistry of the
Metal-Carbon Bond; Hartley, F. R., Patai, S., Eds.; Wiley: New York,
1985; Vol. 2, p 625.
(11) Weinberg, E. L.; Hunter, B. K.; Baird, M. C. J. Organomet. Chem.
1982, 240, 95.
(12) (a) Ryabov, A. D.; Eliseev, A. V.; Yateimirsky, A. K. Appl. Organomet.
Chem. 1988, 2, 19. (b) Kurosawa, H.; Emoto, M.; Kawasaki,
Y. J. Organomet. Chem. 1988, 346, 137.
(13) Catellani, M.; Chiusoli, G. P. J. Organomet. Chem. 1988,346, C27.
Catellani, M.; Mann, B. E. J. Organomet. Chem. 1990,390, 251.
(14) Diversi, P.; Fasce, D.; Santini, R. J. Organomet. Chem. 1984,269,
285.
(15) (a) Maassarani, F.; Pfeffer, M.; Le Borgne, G.; Jastrzebski, J. T.
B. H.; van Koten, G. Organometallics 1987, 6, 1111. (b) Cornioley-
Deuschel, C.; von Zelewsky, A. Inorg. Chem. 1987,26, 3354.
(16) Byers, P. K.; Canty, A. J.; Skelton, B. W.; White, A. H. J. Chem.
SOC.,C hem. Commun. 1986, 1722.
(17) Byers, P. K.; Canty, A. J.; Skelton, B. W.; White, A. H. Organometallics
1990, 9, 826.
(18) Byers, P. K.; Canty, A. J.; Traill, P. R.; Watson, A. A. J. Organomet.
Chem. 1990,390,399.
(19) de Graaf, W.; Boersma, J.; Smeets, W. J. J.; Spek, A. L.; van
Koten, G. Organometallics 1989, 8, 2907.
(20) de Graaf, W.; Boersma, J.; van Koten, G. Organometallics 1990,
9, 1479.
(21) Canty, A. J.; Watson, A. A.; Skelton, B. W.; White, A. H. J.
Organomet. Chem. 1989, 367, C25.
(22) Byers, P. K.; Canty, A. J.; Honeyman, R. T.; Watson, A. A. J.
Organomet. Chem. 1990, 385, 429.
(23) Albano, V. G.; Castellari, C.; Cucciolito, M. E.; Panunzi, A,; Vitagliano,
A. Organometallics 1990, 9, 1269.
(24) Canty, A. J.; Watson, A. A. Inorg. Chim. Acta 1988, 154, 5.
(25) Byers, P. K.; Canty, A. J. J. Chem. SOC.C, hem. Commun. 1988,
(26) Aye, K.-T.; Canty, A. J.; Crespo, M.; Puddephatt, R. J.; Scott, J.
(27) Byers, P. K.; Canty, A. J. Organometallics 1990, 9, 210.
D.; Watson, A. A. Organometallics 1989,8, 1518.
(28) Clark, R. J. H.; Croud, V. 9.;D awes, H. M.; Hursthouse, M. 9.
Polyhedron 1988, 24, 2611.
9) Brown, D. G.; Byers, P. K.; Canty, A. J. Organometallics 1990,
(30) Byers, P. K.; Canty, A. J.; Crespo, M.; Puddephatt, R. J.; Scott,
(31) Monaghan, P. K.; Puddephatt, R. J. Organometallics 1985, 4,
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(32) Scott, J. D.; Crespo, M.; Anderson, C.; Puddephatt, R. J. Or-
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ganometallics 1987, 6, 1772.
1988,595.
(34) See e.g.: Clegg, D. E.; Hall, J. R.; Swile, G. A. J. Orgonomet.
(35) Crespo, M.; Puddephatt, R. J. Organometallics 1987, 6, 2548.
(36) Byers, P. K.; Canty, A. J.; Engelhardt, L. M.; White, A. H. J.
(37) Perrin, D. D.; Armarego, W. L. F.; Perrin, 0. R. Purification of
Chem. SOC., Dalton Trans. 1986, 1731.
Laboratory Chemicals, 2nd ed.; Pergamon: Oxford, England, 1980.
(38) Ibere, J. A,, Hamilton, W. C., Eds. International Tables for XRay
Crystallography; Kynoch Press: Birmingham, England, 1974; Vol.
4.
2.4; Universities of Western Australia and Maryland, 1988.
(39) Hall, S. R., Stewart, J. M., Eds. XTAL User's Manual-" name="eprints.referencetext" />
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<meta content="N-Methylimidazolyllithium reacts with N-methylimidazole-2-carbaldehyde to form bis(N-methylimidazol-2-yl)methanol, and with the esters ethyl N-methylimidazole-2-carboxylate and ethyl pyridine-2-carboxylate to give bis(N-methylimidazol-2-yl)methanone, (mim)2CO, and (N-methylimidazol-2-yl)(pyridin-2-yl)methanone, (Py)(mim)CO, respectively. The ketones react with
N-methylimidazolyllithium to give tris(N-methylimidazol-2-yl)methanol,(mim)3COH, and bis(N-methylimidazol-
2-yl)(pyridin-2-y1)methanol(Py)(mim)2COH, respectively." name="DC.description" />
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<h1 class="ep_tm_pagetitle">Synthesis of Ketones and Methanols Containing Pyridinyl and N-Methylimidazolyl Groups</h1>
<p style="margin-bottom: 1em" class="not_ep_block"><span class="person_name">Canty, A.J.</span> and <span class="person_name">George, E.E.</span> and <span class="person_name">Lee, C.V.</span> (1983) <xhtml:em>Synthesis of Ketones and Methanols Containing Pyridinyl and N-Methylimidazolyl Groups.</xhtml:em> Australian Journal of Chemistry, 36 (2). pp. 415-418. ISSN 0004-9425</p><p style="margin-bottom: 1em" class="not_ep_block"></p><table style="margin-bottom: 1em" class="not_ep_block"><tr><td valign="top" style="text-align:center"><a href="http://eprints.utas.edu.au/2848/1/AJC1983_2C_415.pdf"><img alt="[img]" src="http://eprints.utas.edu.au/style/images/fileicons/application_pdf.png" class="ep_doc_icon" border="0" /></a></td><td valign="top"><a href="http://eprints.utas.edu.au/2848/1/AJC1983_2C_415.pdf"><span class="ep_document_citation">PDF</span></a> - Full text restricted - Requires a PDF viewer<br />196Kb</td><td><form method="get" accept-charset="utf-8" action="http://eprints.utas.edu.au/cgi/request_doc"><input accept-charset="utf-8" value="4060" name="docid" type="hidden" /><div class=""><input value="Request a copy" name="_action_null" class="ep_form_action_button" onclick="return EPJS_button_pushed( '_action_null' )" type="submit" /> </div></form></td></tr></table><p style="margin-bottom: 1em" class="not_ep_block">Official URL: <a href="http://www.publish.csiro.au/nid/51/paper/CH9830415.htm">http://www.publish.csiro.au/nid/51/paper/CH9830415.htm</a></p><div class="not_ep_block"><h2>Abstract</h2><p style="padding-bottom: 16px; text-align: left; margin: 1em auto 0em auto">N-Methylimidazolyllithium reacts with N-methylimidazole-2-carbaldehyde to form bis(N-methylimidazol-2-yl)methanol, and with the esters ethyl N-methylimidazole-2-carboxylate and ethyl pyridine-2-carboxylate to give bis(N-methylimidazol-2-yl)methanone, (mim)2CO, and (N-methylimidazol-2-yl)(pyridin-2-yl)methanone, (Py)(mim)CO, respectively. The ketones react with
N-methylimidazolyllithium to give tris(N-methylimidazol-2-yl)methanol,(mim)3COH, and bis(N-methylimidazol-
2-yl)(pyridin-2-y1)methanol(Py)(mim)2COH, respectively.</p></div><table style="margin-bottom: 1em" cellpadding="3" class="not_ep_block" border="0"><tr><th valign="top" class="ep_row">Item Type:</th><td valign="top" class="ep_row">Article</td></tr><tr><th valign="top" class="ep_row">Subjects:</th><td valign="top" class="ep_row"><a href="http://eprints.utas.edu.au/view/subjects/250300.html">250000 Chemical Sciences > 250300 Organic Chemistry</a></td></tr><tr><th valign="top" class="ep_row">ID Code:</th><td valign="top" class="ep_row">2848</td></tr><tr><th valign="top" class="ep_row">Deposited By:</th><td valign="top" class="ep_row"><span class="ep_name_citation"><span class="person_name">Prof Allan J Canty</span></span></td></tr><tr><th valign="top" class="ep_row">Deposited On:</th><td valign="top" class="ep_row">11 Jan 2008 15:32</td></tr><tr><th valign="top" class="ep_row">Last Modified:</th><td valign="top" class="ep_row">11 Jan 2008 15:32</td></tr><tr><th valign="top" class="ep_row">ePrint Statistics:</th><td valign="top" class="ep_row"><a target="ePrintStats" href="/es/index.php?action=show_detail_eprint;id=2848;">View statistics for this ePrint</a></td></tr></table><p align="right">Repository Staff Only: <a href="http://eprints.utas.edu.au/cgi/users/home?screen=EPrint::View&eprintid=2848">item control page</a></p>
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