title: Transition-metal-free synthesis of aryl-substituted tert-butyl ynol ethers through addition/elimination substitution at an sp centre.
abstract: Nucleophilic attack of an alkoxide on an alkynyl sulfonamide leads to displacement of the sulfonamide at the sp centre and isolation of the ynol ether in good yield in a single operation. The mechanistic pathway has been probed by the use of coordinating additives, (13)C-labelling experiments and ab initio calculations, which indicated that an addition/elimination mechanism is in operation.
authors.affiliation: Department of Chemistry, University College London, UK.
authors.forename: Vincent J
authors.initials: VJ
authors.lastname: Gray
authors.forename: Ben
authors.initials: B
authors.lastname: Slater
authors.forename: Jonathan D
authors.initials: JD
authors.lastname: Wilden
mesh_terms: D000480:Alkynes / Q000737:chemistry*; D002247:Carbon Isotopes / Q000737:chemistry*; D004987:Ethers / Q000138:chemical synthesis* / Q000737:chemistry; D011789:Quantum Theory; D013449:Sulfonamides / Q000737:chemistry*; D028561:Transition Elements; D020002:tert-Butyl Alcohol / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D000480:Alkynes; D002247:Carbon Isotopes; D004987:Ethers; D013449:Sulfonamides; D028561:Transition Elements; D020002:tert-Butyl Alcohol