title: Tandem RCM-Claisen rearrangement-[2+2] cycloaddition of O,O'-(but-2-en-1,4-diyl)-bridged binaphthols.
abstract: Attempted RCM of 2,2'-bis(allyloxy)-1,1'-binaphthyl resulted in a Claisen-type rearrangement of a postulated labile dioxacyclodecine proceeding at room temperature and followed by [2+2] cycloaddition. Structures of products were confirmed by X-ray crystallography. A mechanistic rationalisation based on relative stabilities of proposed intermediates and transition states is provided.
authors.affiliation: Faculty of Chemistry, Institute of Organic Chemistry, University of Vienna, Währinger Straße 38, A-1090 Wien, Austria.
authors.forename: Michael
authors.initials: M
authors.lastname: Abraham
authors.forename: Wolfgang
authors.initials: W
authors.lastname: Reischl
authors.forename: Karl A
authors.initials: KA
authors.lastname: Kirchner
authors.forename: Alexander
authors.initials: A
authors.lastname: Roller
authors.forename: Luis F
authors.initials: LF
authors.lastname: Veiros
authors.forename: Michael
authors.initials: M
authors.lastname: Widhalm
mesh_terms: D018360:Crystallography, X-Ray; D061565:Cycloaddition Reaction; D008958:Models, Molecular; D015394:Molecular Structure; D009281:Naphthalenes / Q000138:chemical synthesis / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D009281:Naphthalenes; C412330:1,1'-binaphthyl