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<title>UTas ePrints - Organopalladium(IV) Chemistry: Oxidative Addition of Organohalides to Dimethylpalladium(ii) Complexes to form Ethyl, sigma-Benzyl, and sigma-Allylpalladium(IV) Complexes</title>
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<meta content="Canty, A.J." name="eprints.creators_name" />
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<meta content="Allan.Canty@utas.edu.au" name="eprints.creators_id" />
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<meta content="The first examples of ethyl, sigma-benzyl, and sigma-allylpalladium(IV) complexes are formed on oxidative addition of organo ha1ides to PdMe2{(pyrid in-2-yl)bis(N-methyIimidazoI-2-yl)methane} [PdMe2{(py)(mim)2CH}]; the complexes [fac-PdRMe2{(py)(mim)2CH-N,N',N"}]X (RX = Etl, PhCH2Br, CH2=CHCH2Br) are stable at ambient temperature, with the cations present as two isomers, and benzyl bromide also forms the neutral complex fac-Pd(CH2Ph)Me2(bipy)Br on oxidative addition to PdMe2(2,2'-bipyridyl), but Etl and CH2=CHCH2Br form transient Pd(IV) species, detectable by 1H n.m.r. spectroscopy, prior to reductive elimination reactions." name="eprints.abstract" />
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References
1 W. J. Pope and S. J. Peachey, Proc. Chem. SOC., 1907, 23, 86;
J. Chem. SOC., 1909, 571.
2 R. Uson, J. Fornies, and R. Navarro, Synth. React. Znorg.
Metal-Org. Chem., 1977, 7,235; J . Organomet. Chem., 1975,96,
307.
3 P. K. Byers, A. J. Canty, B. W. Skelton, and A. H. White,
J. Chem. SOC., Chem. Commun., 1986, 1722.
4 P. K. Byers, A. J. Canty, B. W. Skelton, and A. H. White,
5 P. K. Byers, A. J. Canty, B. W. Skelton, and A. H. White,
6 G. R. Newkome, V. K. Gupta, H. C. R. Taylor, and F. R.
7 A. J. Canty, N. Chaichit, B. M. Gatehouse, E. E. George, and
8 A. J. Canty and C. V. Lee, Organometallics, 1982, 1, 1063.
9 P. K. Byers and A. J. Canty, Znorg. Chim. Acta, 1985, 104, L13.
10 G. Paiaro and A. MUSCOT, etrahedron Lett., 1965, 1583.
11 B. Akermark, B. Krakenberger, S. Hansson, and A. Vitagliano,
Organometallics, 1987, 6, 620.
12 L. S. Hegedus, B. Akermark, D. J. Olsen, 0. P. Anderson, and
K. Zetterberg, J. Am. Chem. SOC., 1982, 104, 697.
13 For a recent report proposing undetected organopalladium(1v)
intermediates, see, for example, a report of the coupling of
acetylenes to form enynes: B. M. Trost, C. Chan, and G. Ruhter,
J. Am. Chem. SOC., 1987, 109, 3486.
14 D. Milstein and J. K. Stille, J. Am. Chem. SOC., 1979, 101, 4992;
A. Gillie and J. K. Stille, ibid., 1980, 102, 4933; M. K. Loar and
J. K. Stille, ibid., 1981, 103, 4174; A. Moravskiy and J. K. Stille,
ibid., 1981, 103, 4182." name="eprints.referencetext" />
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<h1 class="ep_tm_pagetitle">Organopalladium(IV) Chemistry: Oxidative Addition of Organohalides to Dimethylpalladium(ii) Complexes to form Ethyl, sigma-Benzyl, and sigma-Allylpalladium(IV) Complexes</h1>
<p style="margin-bottom: 1em" class="not_ep_block"><span class="person_name">Byers, P.K.</span> and <span class="person_name">Canty, A.J.</span> (1988) <xhtml:em>Organopalladium(IV) Chemistry: Oxidative Addition of Organohalides to Dimethylpalladium(ii) Complexes to form Ethyl, sigma-Benzyl, and sigma-Allylpalladium(IV) Complexes.</xhtml:em> Journal of the Chemical Society, Chemical Communications, 10 . pp. 639-641. ISSN 1359-7345</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/2825/1/CC1988_2C_639.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/2825/1/CC1988_2C_639.pdf"><span class="ep_document_citation">PDF</span></a> - Full text restricted - Requires a PDF viewer<br />291Kb</td><td><form method="get" accept-charset="utf-8" action="http://eprints.utas.edu.au/cgi/request_doc"><input accept-charset="utf-8" value="4026" 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://dx.doi.org/10.1039/C39880000639">http://dx.doi.org/10.1039/C39880000639</a></p><div class="not_ep_block"><h2>Abstract</h2><p style="padding-bottom: 16px; text-align: left; margin: 1em auto 0em auto">The first examples of ethyl, sigma-benzyl, and sigma-allylpalladium(IV) complexes are formed on oxidative addition of organo ha1ides to PdMe2{(pyrid in-2-yl)bis(N-methyIimidazoI-2-yl)methane} [PdMe2{(py)(mim)2CH}]; the complexes [fac-PdRMe2{(py)(mim)2CH-N,N',N"}]X (RX = Etl, PhCH2Br, CH2=CHCH2Br) are stable at ambient temperature, with the cations present as two isomers, and benzyl bromide also forms the neutral complex fac-Pd(CH2Ph)Me2(bipy)Br on oxidative addition to PdMe2(2,2'-bipyridyl), but Etl and CH2=CHCH2Br form transient Pd(IV) species, detectable by 1H n.m.r. spectroscopy, prior to reductive elimination reactions.</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/259901.html">250000 Chemical Sciences > 259900 Other Chemical Sciences > 259901 Organometallic Chemistry</a></td></tr><tr><th valign="top" class="ep_row">ID Code:</th><td valign="top" class="ep_row">2825</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 11:18</td></tr><tr><th valign="top" class="ep_row">Last Modified:</th><td valign="top" class="ep_row">11 Jan 2008 11:18</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=2825;">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=2825">item control page</a></p>
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