title: Stereoselective synthesis of beta-(chloro)vinylsilanes using a regio- and (E)-stereoselective bis-stannylation of unsymmetrically substituted butadiynes: application to the synthesis of a masked triyne.
abstract: [reaction: see text] A highly regio- and stereoselective bis-stannylation of unsymmetrically substituted butadiyne 3 provides bis-stannane 4. Selective lithiation of the internal tin residue effects a 1,4-retro-Brook rearrangement to afford vinylsilane 5. This was elaborated into the novel diethynylethene 1, which also functions as a masked triyne.
authors.affiliation: School of Chemistry, University of Birmingham, Edgbaston, Birmingham B15 2TT, UK.
authors.forename: Simon M E
authors.initials: SM
authors.lastname: Simpkins
authors.forename: Benson M
authors.initials: BM
authors.lastname: Kariuki
authors.forename: Caterina S
authors.initials: CS
authors.lastname: Aricó
authors.forename: Liam R
authors.initials: LR
authors.lastname: Cox