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Article: Combinative use of high-pressure, metal-templating and sulfur- nucleophilicity towards dithiacyclophane synthesis and its complex intermediates

TitleCombinative use of high-pressure, metal-templating and sulfur- nucleophilicity towards dithiacyclophane synthesis and its complex intermediates
Authors
KeywordsDithiacyclophane
Template
Sulfide
Platinum
Nucleophilicity
High-pressure
Issue Date2006
Citation
Journal of Organometallic Chemistry, 2006, v. 691, n. 3, p. 349-355 How to Cite?
AbstractCombined use of elevated pressure in the liquid phase (15 kbar), a metal template and the sulfur nucleophilicity of [Pt2(μ-S) 2(P-P)2] (P-P = diphosphine or 2 • monophosphine) facilitates the one-pot synthesis of 3,8-dibenzo-1,6-dithiacyclodecane. Under r.t.p., nucleophilic addition of [Pt2(μ-S)2(P-P) 2] [P-P = 2 • PPh3; Ph2P(CH 2)nPPh2, n = 2, 1,2-bis(diphenylphosphino) ethane (dppe), 3, 1,3-bis(diphenylphosphino)propane (dppp)] with α-α′-dichloro-o-xylene would terminate as a dithiolato bridged cation viz. [Pt2(μ-SCH2C6H 4CH2S)(P-P)2]2+. Under high pressure (15 kbar) at r.t., these stoichiometric reactions progress via a "catalytic-like" pathway to yield 3,8-dibenzo-1,6-dithiacyclodecane (up to 35%), and a series of mechanistically relevant intermediates and byproducts. The dithiolated intermediates [Pt2(μ-SCH 2C6H4CH2S)(P-P)2] 2+ for PPh3 and dppp have been isolated as PF6- complexes and their crystal structure determined. The formation of 3,8-dibenzo-1,6- dithiacyclodecane demonstrates a convenient synthetic strategy over the multi-step synthesis of this macrocyclic dithioether. © 2005 Elsevier B.V. All rights reserved.
Persistent Identifierhttp://hdl.handle.net/10722/237568
ISSN
2023 Impact Factor: 2.1
2023 SCImago Journal Rankings: 0.359
ISI Accession Number ID

 

DC FieldValueLanguage
dc.contributor.authorChong, Siew Huay-
dc.contributor.authorYoung, David J.-
dc.contributor.authorAndy Hor, T. S.-
dc.date.accessioned2017-01-16T06:09:50Z-
dc.date.available2017-01-16T06:09:50Z-
dc.date.issued2006-
dc.identifier.citationJournal of Organometallic Chemistry, 2006, v. 691, n. 3, p. 349-355-
dc.identifier.issn0022-328X-
dc.identifier.urihttp://hdl.handle.net/10722/237568-
dc.description.abstractCombined use of elevated pressure in the liquid phase (15 kbar), a metal template and the sulfur nucleophilicity of [Pt2(μ-S) 2(P-P)2] (P-P = diphosphine or 2 • monophosphine) facilitates the one-pot synthesis of 3,8-dibenzo-1,6-dithiacyclodecane. Under r.t.p., nucleophilic addition of [Pt2(μ-S)2(P-P) 2] [P-P = 2 • PPh3; Ph2P(CH 2)nPPh2, n = 2, 1,2-bis(diphenylphosphino) ethane (dppe), 3, 1,3-bis(diphenylphosphino)propane (dppp)] with α-α′-dichloro-o-xylene would terminate as a dithiolato bridged cation viz. [Pt2(μ-SCH2C6H 4CH2S)(P-P)2]2+. Under high pressure (15 kbar) at r.t., these stoichiometric reactions progress via a "catalytic-like" pathway to yield 3,8-dibenzo-1,6-dithiacyclodecane (up to 35%), and a series of mechanistically relevant intermediates and byproducts. The dithiolated intermediates [Pt2(μ-SCH 2C6H4CH2S)(P-P)2] 2+ for PPh3 and dppp have been isolated as PF6- complexes and their crystal structure determined. The formation of 3,8-dibenzo-1,6- dithiacyclodecane demonstrates a convenient synthetic strategy over the multi-step synthesis of this macrocyclic dithioether. © 2005 Elsevier B.V. All rights reserved.-
dc.languageeng-
dc.relation.ispartofJournal of Organometallic Chemistry-
dc.subjectDithiacyclophane-
dc.subjectTemplate-
dc.subjectSulfide-
dc.subjectPlatinum-
dc.subjectNucleophilicity-
dc.subjectHigh-pressure-
dc.titleCombinative use of high-pressure, metal-templating and sulfur- nucleophilicity towards dithiacyclophane synthesis and its complex intermediates-
dc.typeArticle-
dc.description.naturelink_to_subscribed_fulltext-
dc.identifier.doi10.1016/j.jorganchem.2005.08.055-
dc.identifier.scopuseid_2-s2.0-29344447486-
dc.identifier.volume691-
dc.identifier.issue3-
dc.identifier.spage349-
dc.identifier.epage355-
dc.identifier.isiWOS:000234614500010-
dc.identifier.issnl0022-328X-

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