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Řádek 1:
{{Pracuje se}}
 
'''Organokovová chemie prvků 2. skupiny''' označuje odvětví [[organokovová chemie|organokovové chemie]] zabývající se sloučeninami obsahujícími [[chemická vazba|chemické vazby]] mezi atomy [[uhlík]]u a některého z&nbsp;prvků [[kovy alkalických zemin|2.&nbsp;skupiny]] periodické tabulky.<ref>''Comprehensive Organometallic Chemistry'' by Mike Mingos, Robert Crabtree '''2007''' {{ISBN|978-0-08-044590-8}}</ref><ref>C. Elschenbroich, A. Salzer ''Organometallics : A Concise Introduction'' (2nd Ed) ('''1992''') from Wiley-VCH: Weinheim. {{ISBN|3-527-28165-7}}</ref> Nejběžnějšími takovými sloučeninami jsou [[Grignardovo činidlo|Grignardova činidla]], obsahující vazby uhlík-[[hořčík]], široce používaná v&nbsp;[[organická chemie|organické chemii]]. Organokovové sloučeniny ostatních prvků této skupiny jsou vzácné a většinou je jeich využití omezeno na chemický výzkum.
 
Řádek 14 ⟶ 12:
Alkyl- a arylhalogenidy s&nbsp;jednou vazbou C-M a jednou vazbou C-X se obvykle řipravují [[oxidační adice|oxidačními adicemi]]. Sloučeniny tohoto druhu obsahující hořčík jsou známy jako [[Grignardovo činidlo|Grignardova činidla]]; některé jejich vápenaté analogy jsou reaktivnější a více citlivé na rozklad. Vápenatá Grignardova činidla musí být předem aktivována.<ref>{{cite journal|title=Highly Reactive Calcium for the Preparation of Organocalcium Reagents: 1-Adamantyl Calcium Halides and Their Addition to Ketones: 1-(1-Adamantyl)cyclohexanol|authors=Reuben D. Rieke, Tse-Chong Wu, Loretta I. Rieke|journal=Org. Synth.|year=1995|volume=72|page=147|doi=10.15227/orgsyn.072.0147}}</ref>
 
NžeNíže jsou uvedeny základní postupy přípravy dialkylových a diarylových sloučenin prvků 2.&nbsp;skupiny:
 
*[[Podvojná záměna]]:
Řádek 31 ⟶ 29:
Organoberyllnaté sloučeniny se často připravují [[alkylace|alkylací]] [[chlorid berylnatý|chloridu berylnatého]].<ref name=naglav>''Off the Beaten Track—A Hitchhiker's Guide to Beryllium Chemistry'' D. Naglav, M. R. Buchner, G. Bendt, F. Kraus, S. Schulz, Angew. Chem. Int. Ed. 2016, 55, 10562. {{DOI|10.1002/anie.201601809}}</ref> Ke známým organoberyllnatýmn sloučeninám poatří například dineopentylberyllium,<ref>{{cite journal|doi=10.1039/J19710001308|title=Preparation of base-free beryllium alkyls from trialkylboranes. Dineopentylberyllium, bis(trimethylsilylmethyl)beryllium, and an ethylberyllium hydride|year=1971|last1=Coates|first1=G. E.|last2=Francis|first2=B. R.|journal=Journal of the Chemical Society A: Inorganic, Physical, Theoretical|pages=1308}}</ref> beryllocen (Cp<sub>2</sub>Be),<ref>{{cite journal|doi=10.1002/cber.19590920233|title=Über Aromatenkomplexe von Metallen, XXV. Di-cyclopentadienyl-beryllium|year=1959|last1=Fischer|first1=Ernst Otto|last2=Hofmann|first2=Hermann P.|journal=Chemische Berichte|volume=92|pages=482|issue=2}}</ref><ref>{{cite journal|doi=10.1071/CH9841601|title=A precise low-temperature crystal structure of Bis(cyclopentadienyl)beryllium|year=1984|last1=Nugent|first1=KW|last2=Beattie|first2=JK|last3=Hambley|first3=TW|last4=Snow|first4=MR|journal=Australian Journal of Chemistry|volume=37|pages=1601|issue=8}}</ref><ref>{{cite journal|doi=10.1016/S0022-328X(00)92065-5|title=The molecular structure of beryllocene, (C5H5)2Be. A reinvestigation by gas phase electron diffraction|year=1979|last1=Almenningen|first1=A|journal=Journal of Organometallic Chemistry|volume=170|pages=271|issue=3|last2=Haaland|first2=Arne|last3=Lusztyk|first3=Janusz}}</ref><ref>{{cite journal|doi=10.1107/S0567740872004820|title=Crystal structure of bis(cyclopentadienyl)beryllium at −120&nbsp;°C|year=1972|last1=Wong|first1=C. H.|last2=Lee|first2=T. Y.|last3=Chao|first3=K. J.|last4=Lee|first4=S.|journal=[[Acta Crystallographica|Acta Crystallographica Section B]]|volume=28|pages=1662|issue=6|doi-access=free}}</ref> diallylberyllium (získávané reakcí diethylberyllia s&nbsp;triallylboranem),<ref>{{cite journal|doi=10.1002/zaac.19744050111|title=Ein Beitrag zur Existenz von Allylberyllium- und Allylaluminiumverbindungen|year=1974|last1=Wiegand|first1=G.|last2=Thiele|first2=K.-H.|journal=Zeitschrift für anorganische und allgemeine Chemie|volume=405|pages=101}}</ref> bis(1,3-trimethylsilylallyl)beryllium<ref>{{cite journal|doi=10.1002/anie.201001866|pmid=20575128|title=Bis(1,3-trimethylsilylallyl)beryllium|year=2010|last1=Chmely|first1=Stephen C.|last2=Hanusa|first2=Timothy P.|last3=Brennessel|first3=William W.|journal=[[Angewandte Chemie|Angewandte Chemie International Edition]]|volume=49|issue=34|pages=5870–4}}</ref> a Be(mes)2.<ref name=naglav/><ref>''Synthesis and structural characterization of the beryllium compounds [Be(2,4,6-Me3C6H2)2(OEt2)], [Be{O(2,4,6-tert-Bu3C6H2)}2(OEt2)], and [Be{S(2,4,6-tert-Bu3C6H2)}2(THF)].cntdot.PhMe and determination of the structure of [BeCl2(OEt2)2]'' Karin Ruhlandt-Senge, Ruth A. Bartlett, Marilyn M. Olmstead, and Philip P. Power Inorganic Chemistry 1993 32 (9), 1724-1728 {{DOI|10.1021/ic00061a031}}</ref> Ligandy zde mohou být i [[aryl]]ové<ref>{{cite journal|doi=10.1021/ic00061a031|title=Synthesis and structural characterization of the beryllium compounds [Be(2,4,6-Me<sub>3</sub>C<sub>6</sub>H<sub>2</sub>)<sub>2</sub>(OEt<sub>2</sub>)], [Be{O(2,4,6-tert-Bu<sub>3</sub>C<sub>6</sub>H<sub>2</sub>)}<sub>2</sub>(OEt<sub>2</sub>)], and [Be{S(2,4,6-tert-Bu<sub>3</sub>C<sub>6</sub>H<sub>2</sub>)}<sub>2</sub>(THF)].cntdot.PhMe and determination of the structure of [BeCl<sub>2</sub>(OEt<sub>2</sub>)<sub>2</sub>]|year=1993|last1=Ruhlandt-Senge|first1=Karin|last2=Bartlett|first2=Ruth A.|last3=Olmstead|first3=Marilyn M.|last4=Power|first4=Philip P.|journal=Inorganic Chemistry|volume=32|pages=1724}}</ref> a alkynylové skupiny.<ref>{{cite journal|doi=10.1016/S0022-328X(00)87485-9|title=The crystal structure of dimeric methyl-1-propynyl- beryllium-كس امك trimethylamine|year=1971|last1=Morosin|first1=B|journal=Journal of Organometallic Chemistry|volume=29|pages=7|last2=Howatson|first2=J.}}</ref>
 
== = Organohořečnaté sloučeniny ===
{{podrobně|Grignardovo činidlo}}
<!-- The distinctive feature of the Grignard reagents is their formation from the organic halide and magnesium metal. Most other group II organic compounds are generated by [[salt metathesis]], which limits their accessibility. The formation of the Grignard reagents has received intense scrutiny. It proceeds by a [[single electron transfer|SET]] process. For less reactive organic halides, activated forms of magnesium have been produced in the form of [[Rieke magnesium]]. Examples of Grignard reagents are [[phenylmagnesium bromide]] and [[ethylmagnesium bromide]]. These simplified formulas are deceptive: Grignard reagents generally exist as dietherates, RMgX(ether)2. As such they obey the [[octet rule]].
 
Grignardova činidla se liší od organokovových sloučenin ostatních prvků 2.&nbsp;skupiny tím, že vznikají z&nbsp;[[halogenderiváty|organohalogenidů]] a kovu. Většina organických sloučenin těchto prvků se připravuje podvojnou záměnou, což omezuje jejich dostupnost. Grignardova činidla se připravují pomocí [[jednoelektronový přenos|jednoelektronových přenosů]]. U méně reaktivních organohalogenidů se používají aktivované formy hořčíku připravované ve formě [[Riekeův kov|Riekeova hořčíku]]. Jako příklady Grignardových činidle lze uvést například [[fenylmagnesiumbromid]] a [[ethylmagnesiumbromid]]. Jejich zjednodušené vzorce mohou být zavádějící, protože se tyto sloučeniny obvykle vyskytují jako dietheráty, RMgX(ether)2, a narušují tak [[oktetové pravidlo]].
Grignard reagents participate in the Schlenk equilibrium. Exploiting this reaction is a way to generate [[dimethylmagnesium]]. Beyond Grignard reagents, another organomagnesium compound is [[magnesium anthracene]]. This orange solid is used as a source of highly active magnesium. [[Butadiene]]-magnesium serves as a source for the butadiene dianion. [[Ate complex]]es of magnesium are also well known, e.g LiMgBu<sub>3</sub>.<ref>{{cite journal |doi=10.15227/orgsyn.089.0460|first1=Juan D.|last1=Arredondo|first2=Hongmei|last2=Li|first3=Jaume|last3=Balsells|
 
Grignardova činidla se zapojují do Schlenkovy rovnováhy; pomocí ní se dá získat [[dimethylhořčík]].
 
Mimo Grignardova činidla jsou známy i jiné organohořečnaté sloučeniny, například [[magnesiumanthracen]], což je oranžová pevná látka používaná jako zdroj vysoce aktivního hořčíku. Butadienmagnesium s používá jako zdroj butadienových dianiontů. Rovněž jsou popsány [[Átový komplex|átové komplexy]] hořčíku, jako je LiMgBu<sub>3</sub>.<ref>{{cite journal |doi=10.15227/orgsyn.089.0460|first1=Juan D.|last1=Arredondo|first2=Hongmei|last2=Li|first3=Jaume|last3=Balsells|
title=Preparation of t-Butyl-3-Bromo-5-Formylbenzoate Through Selective Metal-Halogen Exchange Reactions|journal=Organic Syntheses|year=2012|volume=89|page=460|doi-access=free}}</ref>
 
===Organocalcium Organovápník ===
DimethylcalciumDimethylvápník isje obtainedmožné bypřipravit [[Salt metathesis reaction|metathesis]]podvojnou reactionzáměnou ofz&nbsp; [[Metal bisBis(trimethylsilyl)amides|calciumamidy kovů|bis(trimethylsilyl)amideamidu vápenatého]] anda [[methyllithium|methyllithia]] in v&nbsp;[[diethyl etherdiethylether]]u:<ref>"Dimethylcalcium" Benjamin M. Wolf, Christoph Stuhl, Cäcilia Maichle-Mössmer, and Reiner Anwander ''J. Am. Chem. Soc.'' '''2018''', Volume 140, Issue 6, Pages 2373–2383 {{DOI|10.1021/jacs.7b12984}}</ref>
 
:<math>\mathrm{Ca[N\{Si(CH_3 )_3\}_2]_2 + 2\ LiCH_3 \longrightarrow Ca(CH_3)_2 + 2\ Li[N\{Si(CH_3)_3\}_2]}</math>
 
ADalším wellpřípadem known organocalcium compound isje ([[cyclopentadienylcyklopentadienyl|Cp]])calciumvápník(I).{{cn|date=January 2021zdroj?}} Bis(allyl)calciumV&nbsp+;roce was2009 describedbyla inpopsána 2009.příprava bis(allyl)vápníku<ref>"Bis(allyl)calcium" Phillip Jochmann, Thomas S. Dols, Thomas P. Spaniol, Lionel Perrin, Laurent Maron, Jun Okuda ''Angewandte Chemie International Edition'' Volume 48 Issue 31, Pages 5715–5719 2009 {{DOI|10.1002/anie.200901743}}</ref> It forms in a metathesis reaction ofreakcí[allyldraslíku s&nbsp;[[allylpotassium]]jodid andvápenatý|jodidem [[calcium iodidevápenatým]]; as aprodukt stablevytváří non-pyrophoricstabilní off-whitebílý powderprášek:
 
:<chem>\overset{allylpotassium}{2KC3H5} + \overset{calcium\ iodide}{CaI2} ->[\ce{THF}][25^\circ \ce C] {(C3H5)2Ca} + 2KI</chem>
The bonding mode is [[hapticity|η]]<sup>3</sup>. This compound is also reported to give access to an [[hapticity|η]]<sup>1</sup> polymeric (CaCH<sub>2</sub>CHCH<sub>2</sub>)<sub>''n''</sub> compound.<ref>Lichtenberg, C., Jochmann, P., Spaniol, T. P. and Okuda, J. (2011), "The Allylcalcium Monocation: A Bridging Allyl Ligand with a Non-Bent Coordination Geometry". ''Angewandte Chemie International Edition'', 50: 5753–5756. {{doi|10.1002/anie.201100073}}</ref>▼
 
▲TheTato bondingsloučenina modeobsahuje isvazby typu [[hapticityhapticita|η]]<sup>3</sup>. Thisa compoundvmůže istvořit alsopolymer reporteds&nbsp; tohapticitou give access to an [[hapticity|η]]<sup>1</sup> polymeric (CaCH<sub>2</sub>CHCH<sub>2</sub>)<sub>''n''</sub> compound.<ref>Lichtenberg, C., Jochmann, P., Spaniol, T. P. and Okuda, J. (2011), "The Allylcalcium Monocation: A Bridging Allyl Ligand with a Non-Bent Coordination Geometry". ''Angewandte Chemie International Edition'', 50: 5753–5756. {{doi|10.1002/anie.201100073}}</ref>
The compound [(thf)<sub>3</sub>Ca{μ-C<sub>6</sub>H<sub>3</sub>-1,3,5-Ph<sub>3</sub>}Ca(thf)<sub>3</sub>] also described in 2009<ref>"Stable 'Inverse' Sandwich Complex with Unprecedented Organocalcium(I): Crystal Structures of [(thf)2Mg(Br)-C6H2-2,4,6-Ph3] and [(thf)3Ca{μ-C6H3-1,3,5-Ph3}Ca(thf)3]" Sven Krieck, Helmar Görls, Lian Yu, Markus Reiher and Matthias Westerhausen ''[[J. Am. Chem. Soc.]]'', '''2009''', 131 (8), pp 2977–2985 {{DOI|10.1021/ja808524y}}</ref><ref>"Organometallic Compounds of the Heavier s-Block Elements—What Next?" J. David Smith ''[[Angew. Chem. Int. Ed.]]'' '''2009''', 48, 6597–6599 {{DOI|10.1002/anie.200901506}}</ref> is an inverse [[sandwich compound]] with two calcium atoms at either side of an arene.▼
 
▲TheVe compoundstejném roce byla oznámena rovněž příprava [(thf)<sub>3</sub>Ca{μ-C<sub>6</sub>H<sub>3</sub>-1,3,5-Ph<sub>3</sub>}Ca(thf)<sub>3</sub>] also described in 2009,<ref>"Stable 'Inverse' Sandwich Complex with Unprecedented Organocalcium(I): Crystal Structures of [(thf)2Mg(Br)-C6H2-2,4,6-Ph3] and [(thf)3Ca{μ-C6H3-1,3,5-Ph3}Ca(thf)3]" Sven Krieck, Helmar Görls, Lian Yu, Markus Reiher and Matthias Westerhausen ''[[J.Journal Am.of Chem.the Soc.American Chemical Society]]'', '''2009''', 131 (8), pp 2977–2985 {{DOI|10.1021/ja808524y}}</ref><ref>"Organometallic Compounds of the Heavier s-Block Elements—What Next?" J. David Smith ''[[Angew.Angewandte Chem.Chemie|Angewandte Int.Chemie Ed.International Edition]]'' '''2009''', 48, 6597–6599 {{DOI|10.1002/anie.200901506}}</ref> isobrácené ansendvičové inversesloučeniny [[sandwichs&nbsp;atomem compound]]vápníku withna two calcium atoms at either side ofkaždé anstraně arenearenu.
[[Olefin]]s tethered to [[cyclopentadienyl ligand]]s have been shown to coordinate to calcium(II), strontium(II), and barium(II):<ref name=schumann1>{{cite journal | author1 = H. Schumann | author2 = S. Schutte | author3 = H.-J. Kroth | author4= D. Lentz | title = Butenyl-Substituted Alkaline-Earth Metallocenes: A First Step towards Olefin Complexes of the Alkaline-Earth Metals | journal = Angew. Chem. Int. Ed. | year = 2004 | volume = 43 | issue = 45 | pages = 6208–6211 | doi = 10.1002/anie.200460927| pmid = 15549740 }}</ref>▼
 
▲[[OlefinAlkeny]]s tetherednavázané tona [[cyclopentadienylcyklopentadienylové ligandligandy]]s havese beenmohou shownspojovat tos@nbsp;vápenatými, coordinatestrontnatými to calcium(II), strontium(II),a andbarnatými barium(II)ionty:<ref name=schumann1>{{cite journal | author1 = H. Schumann | author2 = S. Schutte | author3 = H.-J. Kroth | author4= D. Lentz | title = Butenyl-Substituted Alkaline-Earth Metallocenes: A First Step towards Olefin Complexes of the Alkaline-Earth Metals | journal = Angew.Angewandte Chem.Chemie Int.International Ed.Edition | year = 2004 | volume = 43 | issue = 45 | pages = 6208–6211 | doi = 10.1002/anie.200460927| pmid = 15549740 }}</ref>
:[[File:Olefine coordination at calcium strontium barium.png|400px|Olefin complexes of calcium, strontium and barium<ref name=schumann1/>]]▼
 
▲:[[FileSoubor:Olefine coordination at calcium strontium barium.png|400px|OlefinAlkenové complexeskomplexy of calciumvápníku, strontiumstroncia anda bariumbarya<ref name=schumann1/>]]
Organocalcium compounds have been investigated as catalysts.<ref>{{cite journal|doi=10.1021/om101063m|title=Cation Charge Density and Precatalyst Selection in Group 2-Catalyzed Aminoalkene Hydroamination|year=2011|last1=Arrowsmith|first1=Merle|last2=Crimmin|first2=Mark R.|last3=Barrett|first3=Anthony G. M.|last4=Hill|first4=Michael S.|last5=Kociok-KöHn|first5=Gabriele|last6=Procopiou|first6=Panayiotis A.|journal=Organometallics|volume=30|issue=6|pages=1493–1506}}</ref>▼
 
▲OrganocalciumOrganovápenaté compoundssloučeniny havebyly beenzkoumány investigatedjako asmožné catalystskatalyzátory.<ref>{{cite journal|doi=10.1021/om101063m|title=Cation Charge Density and Precatalyst Selection in Group 2-Catalyzed Aminoalkene Hydroamination|year=2011|last1=Arrowsmith|first1=Merle|last2=Crimmin|first2=Mark R.|last3=Barrett|first3=Anthony G. M.|last4=Hill|first4=Michael S.|last5=Kociok-KöHn|first5=Gabriele|last6=Procopiou|first6=Panayiotis A.|journal=[[Organometallics]]|volume=30|issue=6|pages=1493–1506}}</ref>
===Organostrontium===
'''Organostrontium''' compounds have been reported as intermediates in [[Barbier reaction|Barbier-type]] reactions.<ref>{{Cite journal| doi = 10.1246/bcsj.77.341| title = The Barbier-Type Alkylation of Aldehydes with Alkyl Halides in the Presence of Metallic Strontium| year = 2004| last1 = Miyoshi | first1 = N.| last2 = Kamiura | first2 = K.| last3 = Oka | first3 = H.| last4 = Kita | first4 = A.| last5 = Kuwata | first5 = R.| last6 = Ikehara | first6 = D.| last7 = Wada | first7 = M.| journal = Bulletin of the Chemical Society of Japan| volume = 77| issue = 2| pages = 341 }}</ref><ref>{{Cite journal| doi = 10.1246/cl.2005.760| title = The Chemistry of Alkylstrontium Halide Analogues: Barbier-type Alkylation of Imines with Alkyl Halides| year = 2005| last1 = Miyoshi | first1 = N.| last2 = Ikehara | first2 = D.| last3 = Kohno | first3 = T.| last4 = Matsui | first4 = A.| last5 = Wada | first5 = M.| journal = Chemistry Letters| volume = 34| issue = 6| pages = 760 }}</ref><ref>{{Cite journal| doi = 10.1002/ejoc.200500484| title = The Chemistry of Alkylstrontium Halide Analogues, Part 2: Barbier-Type Dialkylation of Esters with Alkyl Halides| year = 2005| last1 = Miyoshi | first1 = N.| last2 = Matsuo | first2 = T.| last3 = Wada | first3 = M.| journal = European Journal of Organic Chemistry| volume = 2005| issue = 20| pages = 4253 }}</ref>▼
 
=== Organostroncium ===
[[File:LOMBOF.png|thumb|upright=1.1|Structure of Ba(CH(tms)<sub>2</sub>)<sub>2</sub>(thf)<sub>3</sub> (tms = Si(CH<sub>3</sub>)<sub>3</sub>), with H atoms omitted. Even with bulky alkyl substituents, Ba coordinates to three THF ligands.]]▼
▲'''OrganostrontiumOrganostrontnaté sloučeniny''' compoundsbyly haveidentifikovány beenjako reported as intermediates inmeziprodukty [[BarbierBarbierova reactionreakce|Barbier-typereakcí Barbierova typu]] reactions.<ref>{{Cite journal| doi = 10.1246/bcsj.77.341| title = The Barbier-Type Alkylation of Aldehydes with Alkyl Halides in the Presence of Metallic Strontium| year = 2004| last1 = Miyoshi | first1 = N.| last2 = Kamiura | first2 = K.| last3 = Oka | first3 = H.| last4 = Kita | first4 = A.| last5 = Kuwata | first5 = R.| last6 = Ikehara | first6 = D.| last7 = Wada | first7 = M.| journal = Bulletin of the Chemical Society of Japan| volume = 77| issue = 2| pages = 341 }}</ref><ref>{{Cite journal| doi = 10.1246/cl.2005.760| title = The Chemistry of Alkylstrontium Halide Analogues: Barbier-type Alkylation of Imines with Alkyl Halides| year = 2005| last1 = Miyoshi | first1 = N.| last2 = Ikehara | first2 = D.| last3 = Kohno | first3 = T.| last4 = Matsui | first4 = A.| last5 = Wada | first5 = M.| journal = Chemistry Letters| volume = 34| issue = 6| pages = 760 }}</ref><ref>{{Cite journal| doi = 10.1002/ejoc.200500484| title = The Chemistry of Alkylstrontium Halide Analogues, Part 2: Barbier-Type Dialkylation of Esters with Alkyl Halides| year = 2005| last1 = Miyoshi | first1 = N.| last2 = Matsuo | first2 = T.| last3 = Wada | first3 = M.| journal = European Journal of Organic Chemistry| volume = 2005| issue = 20| pages = 4253 }}</ref>
===Organobarium===
'''Organobarium''' compounds<ref>''Comprehensive organic functional group transformations'' [[Alan R. Katritzky]], Otto Meth-Cohn, [[Charles Rees|Charles Wayne Rees]]</ref> of the type (allyl)BaCl can be prepared by reaction of activated barium (Rieke method [[redox|reduction]] of [[barium iodide]] with lithium biphenylide) with allyl halides.<ref>{{Cite journal| doi = 10.1021/ja00023a058| title = Allylbarium in organic synthesis: unprecedented .alpha.-selective and stereospecific allylation of carbonyl compounds| year = 1991| last1 = Yanagisawa | first1 = A.| last2 = Habaue | first2 = S.| last3 = Yamamoto | first3 = H.| journal = Journal of the American Chemical Society| volume = 113| issue = 23| pages = 8955 }}</ref><ref>{{Cite journal| doi = 10.1021/ja00093a010| title = Allylbarium Reagents: Unprecedented Regio- and Stereoselective Allylation Reactions of Carbonyl Compounds| year = 1994| last1 = Yanagisawa | first1 = A.| last2 = Habaue | first2 = S.| last3 = Yasue | first3 = K.| last4 = Yamamoto | first4 = H.| journal = Journal of the American Chemical Society| volume = 116| issue = 14| pages = 6130 }}</ref> These allylbarium compounds react with carbonyl compounds. Such reagents are more alpha-selective and more stereoselective than the related Grignards or organocalcium compounds. The [[metallocene]] ([[Cp*]])<sub>2</sub>Ba has also been reported.<ref>{{Cite journal | first3 = J. C.| last3 = Huffman| journal = Journal of the Chemical Society, Chemical Communications| issue = 15| pages = 1045 | first2 = T. P.| last2 = Hanusa| title = Solid state structure of bis(pentamethylcyclopentadienyl)barium, (Me5C5)2Ba; the first X-ray crystal structure of an organobarium complex| year = 1988| last1 = Williams | first1 = R. A.| doi = 10.1039/C39880001045 }}</ref>▼
 
▲[[FileSoubor:LOMBOF.png|thumb|upright=1.1|Structure ofStruktura Ba(CH(tms)<sub>2</sub>)<sub>2</sub>(thf)<sub>3</sub> (tms = Si(CH<sub>3</sub>)<sub>3</sub>), withbez Hzobrazení atomsatomů omittedvodíku. EvenI withv&nbsp;případech, bulkykdy alkyljsou substituentsna něj navázány objemné alkylové substituenty, Base coordinatesbaryum tokoordinuje threese třemi [[tetrahydrofuran|THF]] ligandsligandy.]]
===Organoradium===▼
The only known '''organoradium''' compound is the gas-phase [[acetylide]].
 
==See= alsoOrganobaryum ===
▲'''OrganobariumOrganické sloučeniny barya''' compounds<ref>''Comprehensive organic functional group transformations'' [[Alan R. Katritzky]], Otto Meth-Cohn, [[Charles Rees|Charles Wayne Rees]]</ref> of the typedruhu (allyl)BaCl canlze bepřipravit preparedreakcemi byaktivovaného reaction(pomocí ofRiekeho activated barium (Rieke methodmetod [[redoxredoxní reakce|reductionredukce]] of [[bariumjodid iodidebarnatý|jodidu barnatého]] withbifenylidem lithium biphenylidelithným) withbarya allyl halidess&nbsp;allylhalogenidy.<ref>{{Cite journal | doi = 10.1021/ja00023a058| title = Allylbarium in organic synthesis: unprecedented .alpha.-selective and stereospecific allylation of carbonyl compounds| year = 1991| last1 = Yanagisawa | first1 = A.| last2 = Habaue | first2 = S.| last3 = Yamamoto | first3 = H.| journal = Journal of the American Chemical Society| volume = 113| issue = 23| pages = 8955 }}</ref><ref>{{Cite journal| doi = 10.1021/ja00093a010| title = Allylbarium Reagents: Unprecedented Regio- and Stereoselective Allylation Reactions of Carbonyl Compounds| year = 1994| last1 = Yanagisawa | first1 = A.| last2 = Habaue | first2 = S.| last3 = Yasue | first3 = K.| last4 = Yamamoto | first4 = H.| journal = Journal of the American Chemical Society| volume = 116| issue = 14| pages = 6130 }}</ref> TheseAllylbarnaté allylbariumsloučeniny compoundsreagují reacts&nbsp;[[karbonylové with carbonyl compoundssloučeniny|organokarbonyly]]. Vykazují Suchvyšší reagents are more alphaalfa-selectiveselektivitu anda morestereoselektivitu stereoselectivenež thanGrignardova theči relatedorganovápenatá Grignardsčinidla. orTaké organocalciumbyl compounds. Thepopsán [[metalloceneMetaloceny|metalocen]] ([[Pentamethylcyklopentadien|Cp*]])<sub>2</sub>Ba has also been reported.<ref>{{Cite journal | first3 = J. C.| last3 = Huffman| journal = Journal of the Chemical Society, Chemical Communications| issue = 15| pages = 1045 | first2 = T. P.| last2 = Hanusa| title = Solid state structure of bis(pentamethylcyclopentadienyl)barium, (Me5C5)2Ba; the first X-ray crystal structure of an organobarium complex| year = 1988| last1 = Williams | first1 = R. A.| doi = 10.1039/C39880001045 }}</ref>
* [[Organometallic chemistry]]
 
▲=== Organoradium ===
==References== -->
Jedinou známou '''organoradnatou''' sloučeninou je [[acetylidy|acetylid]], identifikovaný v&nbsp;plynném skupenství.
 
== Odkazy ==
 
=== Související články ===
* [[Organokovová chemie]]
 
=== Reference ===
 
{{Překlad | jazyk = en | článek = Group 2 organometallic chemistry | revize = 1037861095}}<references />
 
{{Chemické vazby s uhlíkem}}
 
{{Portály|Chemie}}
 
[[Kategorie:Organokovová chemie]]
Citováno z „https://cs.wikipedia.org/wiki/Organokovová_chemie_prvků_2._skupiny“