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[[Image:OrganotinLogo.png|right|thumb|150px|Organotin compounds are those with tin linked to hydrocarbons.]]
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'''Organotin''' compounds or '''stannanes''' are [[chemical compounds]] based on [[tin]] with [[hydrocarbon]] substituents. Organotin chemistry is part of the wider field of [[organometallic chemistry]].<ref>{{cite journal | title = Synthetic aspects of tetraorganotins and organotin(IV) halides | author = Sander H.L. Thoonen, Berth-Jan Deelman, Gerard van Koten | journal = [[Journal of Organometallic Chemistry]] | issue = 689 | year = 2004 | pages = 2145–2157 | url = http://dspace-test.library.uu.nl/keur/chem/2005-0426-063436/13093.pdf}}</ref> The first organotin compound was diethyltin diiodide ((C<sub>2</sub>H<sub>5</sub>)<sub>2</sub>SnI<sub>2</sub> , ref to. [[Tin]]), discovered by [[Edward Frankland]] in 1849. An organotin compound is commercially applied as a [[hydrochloric acid]] [[scavenger (chemistry)|scavenger]] (or heat stabilizer) in [[polyvinyl chloride]] and as a [[biocide]]. [[Tributyltin oxide]] has been extensively used as a [[wood preservative]]. Tributyltin compounds are used as marine anti-[[biofouling]] agents. Concerns over toxicity<ref>{{cite journal|last=Gajda|first=M.|coauthors=Jancso, A.|year=2010|title=Organotins, formation, use, speciation and toxicology|journal=Metal ions in life sciences|publisher=RSC publishing|location=Cambridge|volume=7, Organometallics in environment and toxicology|isbn=9781847551771}}</ref> of these compounds (some reports describe biological effects to marine life at a concentration of 1 [[nanogram]] per liter) have led to a worldwide ban by the [[International Maritime Organization]]. n-Butyltin trichloride is used in the production of [[tin dioxide]] layers on glass bottles by [[chemical vapor deposition]].
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==Structure of organotin compounds==
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Organotin compounds are generally classified according to their oxidation states.  Tin(IV) compounds are much more common and more useful.


===Organic derivatives of tin(IV)===
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The entire series R<sub>4−''n''</sub>SnCl<sub>''n''</sub> are known for many R groups and values of ''n'' up to 4. Analogous derivatives are known for other halides. [[Alkoxide]] and [[carboxylate]] derivatives however tend to associate and often poorly characterized. The oxides are also complicated.  Many diorganotin oxides, (R<sub>2</sub>SnO)<sub>''n''</sub> are oligomeric:


With bulky R groups, diorganotin oxides adopt cyclic trimeric or dimeric structures consisting of Sn<sub>3</sub>O<sub>3</sub> and Sn<sub>2</sub>O<sub>2</sub> rings, respectively.
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| <center>[[File:R2SnO-cyclic-dimer-2D.png|100px]]</center> ||<center>[[File:R2SnO-cyclic-trimer-2D.png|100px]] </center> || <center>[[File:TBu2SnO-cyclic-trimer-from-xtal-1984-Mercury-3D-balls.png|200px]]</center>||<center>[[File:R2SnO-cross-linked-network-Harris-and-Sebald-1987-2D.png|200px]]</center>
|-
|<center><small>Idealized structure of dimeric diorganotin oxide.</small></center>||<center><small>Idealized structure of trimeric diorganotin oxide.</small></center> || <center><small>Ball-and-stick model for (t-Bu<sub>2</sub>SnO)<sub>3</sub>.</small></center> || <center><small>Structure of diorganotin oxide, highlighting the extensive intermolecular bonding.</small></center>
|}


====Hypercoordinated stannanes====
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Unlike their carbon(IV) analogues but like silicon compounds, tin(IV) can also be [[Coordination compound|coordinated]] to five and even six atoms instead of the regular four. These hypercoordinated compounds usually have [[electronegative]] substituents.  Lithium pentaorganostannates were first detected and characterized in solution in 1986,<ref>{{cite journal | title = Lithium-Metalloid Exchange Reactions. Observation of Lithium Pentaalkyl/aryl Tin Ate Complexes | journal = [[J. Am. Chem. Soc.]] | first2 = Nancy H. | year = 1986 | last2 = Phillips | volume = 108 | pages = 2102 | doi = 10.1021/ja00268a067 | author = Reich, Hans J.}}</ref> while in the subsequent year a six-coordinated tetraorganotin compound was reported.<ref>{{cite journal | title = Synthesis, Spectroscopic Study, and X-ray Crystal Structure of Bis[3-(2-pyridyl)-2-thienyl-C,N]diphenyltin(IV): The First Example of a Six-Coordinate Tetraorganotin Compound | author = V. G. Kumar Das, Lo Kong Mun, Chen Wei, and Thomas C. W. Mak | journal = [[Organometallics]] | year = 1987 | volume = 6 | pages = 10 | doi = 10.1021/om00144a003}}</ref> In 2007 a crystal structure of room-temperature stable (in [[argon]]) all-carbon pentaorganostannane was reported as the [[lithium]] salt with this structure:<ref>{{cite journal | title = Synthesis and Structure of Pentaorganostannate Having Five Carbon Substituents | author = Masaichi Saito, Sanae Imaizumi, Tomoyuki Tajima, Kazuya Ishimura, and Shigeru Nagase | journal = [[J. Am. Chem. Soc.]] | year = 2007 | volume = 129 | pages = 10974–10975 | doi = 10.1021/ja072478}}</ref>


:[[Image:Pentaorganostannane.png|200px|Pentaorganostannane]]
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In this distorted [[Trigonal bipyramid molecular geometry|trigonal bipyramidal structure]] the carbon to tin [[bond length]]s (2.26&nbsp;[[Ångström|Å]] [[Apical (chemistry)|apical]], 2.17&nbsp;Å equatorial) are larger than regular C-Sn bonds (2.14&nbsp;Å) reflecting its [[hypervalency|hypervalent]] nature.
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===Tin radicals (organic derivatives of tin(III))===
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Tin radicals, with the formula R<sub>3</sub>Sn, are called '''stannyl radicals'''.<ref>''Organotin chemistry'' 2004 Alwyn George Davies ISBN 3-527-31023-1</ref> They are invoked as intermediates in certain atom-transfer reactions. For example, [[tributyltin hydride]] (tri-n-butylstannane) serves as a good source of "hydrogen atoms" because of the stability of the tributytin radical.<ref>T. V. RajanBabu, P. C. B. Page B. R. Buckley "Tri-n-butylstannane" in e-EROS Encyclopedia of Reagents for Organic Synthesis, 2004. {{DOI|10.1002/047084289X.rt181.pub2}}</ref>


===Organic derivatives of tin(II)===
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Organotin(II) compounds are somewhat rare. Compounds with the empirical formula SnR<sub>2</sub> are somewhat fragile and exist as rings or polymers when R is not bulky.  The polymers are called [[polystannane]]s and have the formula (SnR<sub>2</sub>)<sub>n</sub>.
:[[Image:Polystannane12.jpg|100px]]


In principle divalent tin compounds might be expected to form analogues of alkenes with a formal [[double bond]]. Indeed compounds with the formula Sn<sub>2</sub>R<sub>4</sub>, called '''distannenes''', are known for certain organic substituents. The Sn centres tend to be highly pyramidal. Monomeric compounds with the formula SnR<sub>2</sub>, analogues of [[carbenes]] are also known in a few cases.  One example is [Sn(SiR<sub>3</sub>]<sub>2</sub> where R = CH(SiMe<sub>3</sub>)<sub>2</sub> (Me = methyl). Such species reversibly dimerize to the distannylene upon crystallization:<ref>{{Holleman&Wiberg}}</ref>
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:2 R<sub>2</sub>Sn  <math>\overrightarrow{\leftarrow}</math> (R<sub>2</sub>Sn)<sub>2</sub>


'''Stannenes''', compounds with tin–carbon double bonds, are exemplified by derivatives of [[stannabenzene]]. [[Stannole]]s, [[structural analog]]s of [[cyclopentadiene]], exhibit little C-Sn double bond character.
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===Organic derivatives of tin(I)===
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Compounds of Sn(I) are rare and only observed with very bulky ligands. One prominent family of cages is accessed by pyrolysis of the 2,6-diethylphenyl-substituted tristannylene [Sn(C<sub>6</sub>H<sub>3</sub>-2,6-Et<sub>2</sub>)<sub>2</sub>]<sub>3</sub>, which affords the [[cubane]] and a [[prismane]]. These cages contain Sn(I) and have the formula [Sn(C<sub>6</sub>H<sub>3</sub>-2,6-Et<sub>2</sub>)]<sub>n</sub> where n = 8, 10.<ref>Lawrence R. Sita "Heavy-Metal Organic Chemistry: Building with Tin" Acc. Chem. Res., 1994, volume 27, pp 191–197.  {{DOI| 10.1021/ar00043a002}}</ref>  A '''stannyne''' contains a carbon to tin [[triple bond]] and a distannyne a triple bond between two tin atoms (RSnSnR). Distannynes only exist for extremely bulky substituents.  Unlike [[alkyne]]s, the C-Sn-Sn-C core of these distannynes are nonlinear, although they are planar.  The Sn-Sn distance is 3.066(1) Å, and the Sn-Sn-C angles are 99.25(14)°. Such compounds are prepared by reduction of bulky aryltin(II) halides.<ref>Philip P. Power "Bonding and Reactivity of Heavier Group 14 Element Alkyne Analogues" Organometallics 2007, volume 26, pp 4362–4372. {{DOI|10.1021/om700365p}}</ref>
[[File:JIMFUG.jpg|340px|thumb|Structure of a Sn<sub>10</sub> prismane, stabilized by bulky 2,6-diethylphenyl substituents.]]
 
== Preparation of organotin compounds ==
Organotin compounds can be synthesised by reaction of a [[Grignard reagent]] with tin halides for example [[tin tetrachloride]]. An example is the [[organic synthesis]] of tributyl-[(Z)-5-phenyl-2-penten-2-yl]stannane:<ref>{{cite journal | title = <nowiki>Tributyl-[(Z)-5-phenyl-2-penten-2-yl]stannane</nowiki> | author = Martin J. Stoermer, John T. Pinhey | journal = [[Molecules (journal)|Molecules]] | year = 1998 | volume = 3 | pages = M67 | url = http://www.mdpi.org/molbank/m0067.htm}}</ref><ref>A [[Grignard reagent]] is prepared from magnesium turnings and (Z)-2-bromo-5-phenyl-2-pentene in dry [[tetrahydrofuran]] and [[titration|titrated]] with [[tributyltin chloride]] until the solution decolourises. The resulting solution is stirred at [[room temperature]] for 1 hour and the solvent is removed in a [[rotavapor]]. [[Diethyl ether]] is added and the ether extract is washed with [[brine]] and filtered and the ether evaporates in a [[rotavapor]]. The crude product is [[kugelrohr]] distilled to yield tributyl-[(Z)-5-phenyl-2-penten-2-yl]stannane as a colourless oil.</ref>
 
:[[Image:Synthesis of organotin compound.png|350px|Synthesis of organotin compound]]
 
The [[Wurtz reaction|Wurtz-like]] coupling of [[organosodium compound|alkyl sodium compounds]] with tin halides yield tetraorganotin compounds. Another method is an [[redistribution reaction]] of tin halides with [[organoaluminium compound]]s (AlR<sub>3</sub>). Triorganotin halides can be prepared in the [[Kocheshkov redistribution reaction]].
 
== Reactions of organotin compounds ==
Important reactions involving organotin compounds are the [[Stille reaction]] (coupling reaction with sp2-hybridized organic halides catalyzed by palladium):
 
:[[Image:Stille reaction scheme.png|500px|Stille reaction scheme]]
 
and [[organostannane addition]]s (nucleophilic addition of an allyl-, allenyl-, or propargylstannanes to an aldehydes and imines). Organotin compounds are also used extensively in [[Radical (chemistry)|radical chemistry]] (e.g. [[radical cyclization]]s, [[Barton–McCombie deoxygenation]], [[Barton decarboxylation]], etc.).
 
== Use and toxicity ==
* Tetraorganotins are very stable molecules with low toxicity and low biological activity. They are unusable as biocides, but they can be metabolized to toxic triorganotin compounds. They are used as starting materials for catalysts.
* Triorganotins are very toxic. Tri-''n''-alkyltins are [[phytotoxic]] and therefore cannot be used in agriculture. Depending on the organic groups, they can be powerful [[bactericide]]s and [[fungicide]]s. [[Tributyltin]]s are used as industrial biocides, e.g. as antifungal agents in textiles and paper, wood pulp and paper mill systems, breweries, and industrial cooling systems.  Tributyltins are also used in marine anti-fouling paint. Triphenyltins are used as active components of antifungal paints and agricultural fungicides. Other triorganotins are used as [[miticide]]s and [[acaricide]]s.
* Diorganotins have no antifungal activity, low toxicity, and low antibacterial activity, except for [[diphenyltin]]s. They are used in polymer manufacturing, as [[Polyvinyl chloride|PVC]] heat stabilizers, catalysts, in the manufacturing of [[polyurethane]] and [[silicone]] curing. [[Dibutyltin oxide|DBT]] is however immunotoxic, and a recent paper suggests a link to auto-immune related diseases.<ref>{{cite journal | author = C Gumy et al. | journal = PLoS ONE | year = 2008 | pages = e3545 | volume = 3 | doi = 10.1371/journal.pone.0003545 | title = Dibutyltin Disrupts Glucocorticoid Receptor Function and Impairs Glucocorticoid-Induced Suppression of Cytokine Production|bibcode = 2008PLoSO...3.3545G }}</ref>
* Monoorganotins have no biocidal activity and their toxicity to mammals is very low. Methyltin, butyltin, octyltin and monoestertins are used as PVC heat stabilizers.
* Many different organotin complexes are being studied in anticancer therapy, observing that their cytotoxicity and selectivity towards cancer cell is higher than that of [[cisplatin]].<ref>{{cite journal | author = S. Gómez-Ruiz et al. | journal = Journal of Inorganic Biochemistry | year = 2008 | volume = 102 | issue = 12 | pmid = 18760840 | pages = 2087 | doi = 10.1016/j.jinorgbio.2008.07.009 | title = Study of the cytotoxic activity of di and triphenyltin(IV) carboxylate complexes}}</ref>
 
== Compounds ==
Organotin compounds are used commercially in a wide range of applications such as biocides, insecticides, chemical intermediates and as catalysts.
<gallery caption="Organotin compounds" perrow="5">
Image:Tetrabutyltin.png|[[Tetrabutyltin]] starting material for the di- and tributyl compounds
Image:Tributyltin oxide.png|[[Tributyltin oxide]], a colorless to pale yellow liquid used in [[wood preservation]]
Image:Fentin acetate.svg|[[Triphenyltin acetate]], an off-white crystalline solid, used as an [[insecticide]] and a [[fungicide]]
Image:Triphenyltin chloride.png|[[Triphenyltin chloride]], a white crystalline solid, used as a biocide and an intermediate in chemical synthesis
Image:Trimethyltin chloride.png|[[Trimethyltin chloride]] also a biocide
Image:Triphenyltin hydroxide.svg|[[Triphenyltin hydroxide]], an off-white powder, used as a [[fungicide]] and to sterilize insects
Image:|[[Fenbutatin oxide]], a very stable white crystalline solid, for control of [[mite]]s
Image:Azocyclotin.png|[[Azocyclotin]], a colorless crystalline solid, used as a long-acting [[acaricide]] for control of [[spider mite]]s on plants
Image:Cyhexatin.svg|[[Cyhexatin]], a white crystalline solid, used as an [[acaricide]] and [[miticide]]
Image:Hexamethylditin.svg|[[Hexamethylditin]] used as an intermediate in chemical synthesis
Image:Tetraethyltin.svg|[[Tetraethyltin]], [[boiling point]] 63–65° /12&nbsp;mm is a catalyst<ref>[[Organic Syntheses]], Coll. Vol. 4, p.881 (1963); Vol. 36, p.86 (1956). [http://www.orgsyn.org/orgsyn/orgsyn/prepContent.asp?prep=cv4p0881 Link]</ref>
</gallery>
 
* [[Tributyltin azide]]
 
== See also ==
* [[Organostannane addition]]
{{ChemicalBondsToCarbon}}
 
== References ==
{{Reflist|2}}
 
== External links ==
* [http://www.npi.gov.au/database/substance-info/profiles/66.html National Pollutant Inventory Fact Sheet for organotins]
* [http://www.ortepa.org/ Industry information site]
* [http://www.chem.wisc.edu/areas/reich/orgmet/tin.htm Organotin chemistry in synthesis]
*[http://newsletter.sgs.com/eNewsletterPro/uploadedimages/000006/SGS-Safeguards-11309-EU-ban-on-Organotin-Compounds-EN-09.pdf EU bans certain organotin compounds in consumer products]
 
{{HealthIssuesOfPlastics}}
 
[[Category:Organotin compounds| ]]

Latest revision as of 12:13, 6 January 2015

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