title: [3,3]-Sigmatropic rearrangement/5-exo-dig cyclization reactions of benzyl alkynyl ethers: synthesis of substituted 2-indanones and indenes.
abstract: Substituted benzyl alkynyl ethers, prepared from the corresponding α-alkoxy ketones in a two-step sequence involving enol triflate formation and KOtBu-induced E2 elimination, undergo [3,3]-sigmatropic rearrangement/intramolecular 5-exo-dig cyclization at 60 °C to form substituted 2-indanones in good overall yields. 1,3-cis-Disubstituted-2-indanones are formed preferentially when the benzylic substituent R(1) is bulky. Substituted indenes may be prepared from 2-indanones in high yields by Horner-Wadsworth-Emmons reaction.
authors.affiliation: Department of Chemistry and Biochemistry, California State University, Northridge 18111 Nordhoff Street, Northridge, California 91330, USA.
authors.forename: Armen A
authors.initials: AA
authors.lastname: Tudjarian
authors.forename: Thomas G
authors.initials: TG
authors.lastname: Minehan
mesh_terms: D000480:Alkynes / Q000737:chemistry*; D003500:Cyclization; D004987:Ethers / Q000737:chemistry*; D007189:Indans / Q000138:chemical synthesis* / Q000737:chemistry*; D007700:Kinetics
chemical_list: D000480:Alkynes; D004987:Ethers; D007189:Indans