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Revision as of 08:59, 18 April 2011 editCheMoBot (talk | contribs)Bots141,565 edits Updating {{chembox}} (no changed fields - added verified revid - updated 'UNII_Ref', 'ChemSpiderID_Ref', 'StdInChI_Ref', 'StdInChIKey_Ref', 'ChEMBL_Ref', 'KEGG_Ref') per Chem/Drugbox validation (← Previous edit Latest revision as of 21:34, 4 January 2025 edit undoDavemck (talk | contribs)Extended confirmed users119,840 editsm Clean up duplicate template arguments using findargdups; fix ref error 
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{{Orphan|date=February 2009}}
{{Chembox {{Chembox
| Verifiedfields = changed
| verifiedrevid = 400838378 | verifiedrevid = 424658175
| ImageFile = Otera's catalyst.JPG | ImageFile = Otera's catalyst.svg
| ImageSize =
| ImageAlt = | ImageSize = 220
| ImageAlt = Skeletal formula of Otera's catalyst
| ImageFile1 = Otera's catalyst 3D ball.png
| ImageSize1 = 260
| ImageAlt1 = Ball-and-stick model of the Otera's catalyst molecule
| IUPACName = | IUPACName =
| PIN = | PIN =
| OtherNames = | OtherNames = Octabutyltetrathiocyanatostannoxane
| Section1 = {{Chembox Identifiers |Section1={{Chembox Identifiers
| CASNo_Ref = {{cascite|changed|??}}
| InChI = 1/8C4H9.2C2HS.2CNS.2O.4Sn/c8*1-3-4-2;2*1-2-3;2*2-1-3;;;;;;/h8*1,3-4H2,2H3;2*1H;;;;;;;;/rC38H74N2O2S4Sn4/c1-9-17-27-47(35-25-43,28-18-10-2)39(37-45)49(31-21-13-5,32-22-14-6)41(47)50(33-23-15-7,34-24-16-8)40(38-46)48(36-26-44,42(49)50,29-19-11-3)30-20-12-4/h35-36H,9-24,27-34H2,1-8H3
⚫ | CASNo = 95971-03-2
| InChIKey = OUBFKIZYHPMZHQ-BIWIHVFOAY
| StdInChI_Ref = {{stdinchicite|correct|chemspider}} | ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
⚫ | ChemSpiderID=17621074
⚫ | StdInChI = 1S/8C4H9.2C2HS.2CNS.2O.4Sn/c8*1-3-4-2;2*1-2-3;2*2-1-3;;;;;;/h8*1,3-4H2,2H3;2*1H;;;;;;;;
⚫ | PubChem = 16689150
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChI_Ref = {{stdinchicite|changed|chemspider}}
⚫ | StdInChIKey = OUBFKIZYHPMZHQ-UHFFFAOYSA-N
⚫ | StdInChI = 1S/8C4H9.4CNS.2O.4Sn/c8*1-3-4-2;4*2-1-3;;;;;;/h8*1,3-4H2,2H3;;;;;;;;;;/q;;;;;;;;4*-1;;;4*+1
⚫ | CASNo =
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}
⚫ | StdInChIKey = BCLBTLOINGPAIT-UHFFFAOYSA-N
⚫ | ChemSpiderID=21106460
⚫ | SMILES = CCCC1(N(=C=S)2(O13(O2(N3=C=S)(CCCC)(CCCC)N=C=S)(CCCC)CCCC)(CCCC)CCCC)(CCCC)N=C=S
⚫ | PubChem =
⚫ | SMILES = CCCC1((=C=S)2(O13(O2(3=C=S)(CCCC)(CCCC)C=C=S)(CCCC)CCCC)(CCCC)CCCC)(CCCC)C=C=S
}} }}
| Section2 = {{Chembox Properties |Section2={{Chembox Properties
| C = 36 | H = 72 | O = 2 | S = 4 | Sn = 4 | N = 4 | C=36 | H=72 | O=2 | S=4 | Sn=4 | N=4
| MolarMass = | MolarMass =
| Appearance = | Appearance =
| Density = | Density =
| MeltingPt = | MeltingPt =
| BoilingPt = | BoilingPt =
| Solubility = }} | Solubility = }}
| Section3 = {{Chembox Hazards |Section3={{Chembox Hazards
| MainHazards = | MainHazards =
| FlashPt = | FlashPt =
| Autoignition = }} | AutoignitionPt = }}
}} }}
'''Otera's catalyst''' is an ] which has been used as a ] catalyst. This isothioscyanate compound is a member of a family of organostannanes reported by Wasada and coworkers,<ref name = wasada>{{cite journal | last1 = Wada | first1 = M | doi = 10.1016/S0022-328X(00)82737-0 | title = Preparation and properties of dialkyltin isothiocyanate derivatives | year = 1965 | pages = 70 | volume = 3 | journal = ]}}</ref> and elaborated upon by Otera and coworkers.<ref name = otera/> '''Otera's catalyst''', named after Japanese chemist Junzo Otera, is an ] which has been used as a ] catalyst. This isothioscyanate compound is a member of a family of organostannanes reported by Wada and coworkers,<ref name = wada>{{cite journal | author1= Wada, M. | author2= Nishino, M. | author3= Okawara, R. | doi = 10.1016/S0022-328X(00)82737-0 | title = Preparation and properties of dialkyltin isothiocyanate derivatives | year = 1965 | pages = 70–75 | volume = 3 | journal = ]}}</ref> and elaborated upon by Otera and coworkers.<ref name = otera>{{cite journal | author=Otera, J| title=Novel template effects of distannoxane catalysts in highly efficient transesterification and esterification | journal=J. Org. Chem. | volume=56 | issue=18 | year=1991 | pages=5307–5311 | doi=10.1021/jo00018a019|display-authors=etal}}</ref>


==Preparation== ==Preparation==
This class of compounds may be prepared generally by the reaction of an organotin halide and oxide:<ref name = otera-chemrev>{{cite journal | last1 = Otera | first1 = Junzo. | title = Transesterification | journal = ] | volume = 93 | pages = 1449 | year = 1993 | doi = 10.1021/cr00020a004}}</ref> This class of compounds may be prepared generally by the reaction of an organotin halide and oxide:<ref name = otera-chemrev>{{cite journal | last1 = Otera | first1 = Junzo. | title = Transesterification | journal = ] | volume = 93 | pages = 1449–1470 | year = 1993 | issue = 4 | doi = 10.1021/cr00020a004}}</ref>


: 2 R<sub>2</sub>SnO + 2 R<sub>2</sub>SnX<sub>2</sub> → (XR<sub>2</sub>SnOSnR<sub>2</sub>X)<sub>2</sub> : 2 R<sub>2</sub>SnO + 2 R<sub>2</sub>SnX<sub>2</sub> → (XR<sub>2</sub>SnOSnR<sub>2</sub>X)<sub>2</sub>


In particular, the thiocyanate compound was prepared by the reaction of dibutyltin oxide with dibutyltin diisothiocyanate.<ref name = wasada/> Otherwise, this compound is not commercially available. In particular, the thiocyanate compound was prepared by the reaction of dibutyltin oxide with dibutyltin diisothiocyanate.<ref name = wada/> Otherwise, this compound is not commercially available.


==Applications== ==Applications==
This thiocyanate compound can be used as a ] ].<ref name = otera>{{cite journal | author=Otera, J ''et al'' | title=Novel template effects of distannoxane catalysts in highly efficient transesterification and esterification | journal=J. Org. Chem. | volume=56 | issue=18 | year=1991 | pages=5307–5311 | doi=10.1021/jo00018a019}}</ref> Although it is not well known, it has been used in a number of total syntheses.<ref>{{cite journal | author=Trost, BM ''et al'' | title=Synthesis of Amphidinolide P | journal=J. Am. Chem. Soc. | volume=127 | year=2005 | pages=17921–17937|doi=10.1055/s-2006-941939 | pmid=16351124 | issue=50 | pmc=2533515}}</ref><ref>{{cite journal | author=Trost, BM; Stiles, DT | title=Total Synthesis of Spirotryprostatin B via Diastereoselective Prenylation | journal=Org. Lett. | year=2007|doi=10.1021/ol070971k | volume=9 | pages=2763 | pmid=17592853 | issue=15}}</ref> This thiocyanate compound can be used as a ] ].<ref name = otera /> Although it is not well known, it has been used in a number of total syntheses.<ref>{{cite journal | author=Trost, BM| title=Synthesis of Amphidinolide P | journal=J. Am. Chem. Soc. | volume=127 | year=2005 | pages=17921–17937|doi=10.1021/ja055967n | pmid=16351124 | issue=50 | pmc=2533515|display-authors=etal}}</ref><ref>{{cite journal |author1=Trost, BM |author2=Stiles, DT | title=Total Synthesis of Spirotryprostatin B via Diastereoselective Prenylation | journal=Org. Lett. | year=2007|doi=10.1021/ol070971k | volume=9 | pages=2763–6 | pmid=17592853 | issue=15}}</ref>


In this application, the reaction occurs via the displacement of the bridging isothiocyanate ligands with the incoming alcohol to form an alcohol-bridged active catalyst. Tin acts as the Lewis acid, and gives the transesterified product.<ref name = otera/><ref name = otera-chemrev/> In this application, the reaction occurs via the displacement of the bridging isothiocyanate ligands with the incoming alcohol to form an alcohol-bridged active catalyst. Tin acts as the ], and gives the transesterified product.<ref name = otera/><ref name = otera-chemrev/> The reaction must be performed in nonpolar solvents in order to colocate the acid and alcohol at the catalytic center.<ref>{{cite blog|archive-url=http://web.archive.org/web/20060727091142/http://blog.tenderbutton.com/?m=20060503|archive-date=27 July 2006|website=Tenderblog|date=3 May 2006|title=falling in love with otera’s catalyst|first=Dylan|last=Stiles|url=http://blog.tenderbutton.com/?m=20060503}}<!--] but subject-matter expert; blog is about PhD at Stanford followed by (AFAICT) Harvard postdoc--></ref>


==References== ==References==
{{reflist}} {{reflist}}



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