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Article: Synthesis of an octamethyl-18-crown-6 derivative and the X-ray crystal structure of its 2:1 complex with borane-ammonia

TitleSynthesis of an octamethyl-18-crown-6 derivative and the X-ray crystal structure of its 2:1 complex with borane-ammonia
Authors
Issue Date1985
Citation
Tetrahedron, 1985, v. 41, n. 14, p. 2923-2926 How to Cite?
AbstractThe synthesis of 2,2,3,3,11,11,12,12-octamethyl-1,4,7,10,13,16-hexaoxacyclooctadecane (2) from pinacol (3) by a sequence of reactions (3→4→5→6+5→2) involving alkylation (3→ 4), ozonolysis and reduction (4→5), tosylation (5→6), and cyclisation (5+6→2) is reported. With borane-ammonia, the octamethyl-18-crown-6 derivative 2 forms a crystalline 2:1 complex, (BH3NH3)2 · 2. X-Ray crystallography reveals the two guest BH3NH3 molecules are hydrogen bonded in a centrosymmetric manner to the opposite faces of the host 2, which adopts an all-gauche (ag+a ag-a)3 conformation. © 1985.
Persistent Identifierhttp://hdl.handle.net/10722/333581
ISSN
2021 Impact Factor: 2.388
2020 SCImago Journal Rankings: 0.581
ISI Accession Number ID

 

DC FieldValueLanguage
dc.contributor.authorAlston, David R.-
dc.contributor.authorStoddart, J. Fraser-
dc.contributor.authorWolstenholme, John B.-
dc.contributor.authorAllwood, Billy L.-
dc.contributor.authorWilliams, David J.-
dc.date.accessioned2023-10-06T05:20:46Z-
dc.date.available2023-10-06T05:20:46Z-
dc.date.issued1985-
dc.identifier.citationTetrahedron, 1985, v. 41, n. 14, p. 2923-2926-
dc.identifier.issn0040-4020-
dc.identifier.urihttp://hdl.handle.net/10722/333581-
dc.description.abstractThe synthesis of 2,2,3,3,11,11,12,12-octamethyl-1,4,7,10,13,16-hexaoxacyclooctadecane (2) from pinacol (3) by a sequence of reactions (3→4→5→6+5→2) involving alkylation (3→ 4), ozonolysis and reduction (4→5), tosylation (5→6), and cyclisation (5+6→2) is reported. With borane-ammonia, the octamethyl-18-crown-6 derivative 2 forms a crystalline 2:1 complex, (BH3NH3)2 · 2. X-Ray crystallography reveals the two guest BH3NH3 molecules are hydrogen bonded in a centrosymmetric manner to the opposite faces of the host 2, which adopts an all-gauche (ag+a ag-a)3 conformation. © 1985.-
dc.languageeng-
dc.relation.ispartofTetrahedron-
dc.titleSynthesis of an octamethyl-18-crown-6 derivative and the X-ray crystal structure of its 2:1 complex with borane-ammonia-
dc.typeArticle-
dc.description.naturelink_to_subscribed_fulltext-
dc.identifier.doi10.1016/S0040-4020(01)96617-7-
dc.identifier.scopuseid_2-s2.0-0002888401-
dc.identifier.volume41-
dc.identifier.issue14-
dc.identifier.spage2923-
dc.identifier.epage2926-
dc.identifier.isiWOS:A1985AMQ4800020-

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