title: Halogenated catechols from cycloaddition reactions of η-(2-ethoxyvinylketene)iron(0) complexes with 1-haloalkynes.
abstract: 1-chloroalkynes and 1-bromohexyne undergo cycloaddition reactions with ethoxyvinylketeneiron(0) complexes to form chloro and bromocatechols. With most substituents, the halogen is incorporated ortho to the phenolic hydroxyl group regioselectively. With chloroethyne, chlorohexyne, and methyl chloropropiolate, the reverse regioselection is observed. Ab initio calculations reveal that the products are, in most cases, nearly isoenergetic, which indicates that the intermediate ketene-alkyne adduct geometry must be important in determining the product distribution.
authors.affiliation: Long Island University, Department of Chemistry and Biochemistry, 1 University Plaza, Brooklyn, New York 11201, USA.
authors.forename: Jimmy
authors.initials: J
authors.lastname: Truong
authors.forename: Vioela
authors.initials: V
authors.lastname: Caze
authors.forename: Ravish K
authors.initials: RK
authors.lastname: Akhani
authors.forename: Gayatribahen K
authors.initials: GK
authors.lastname: Joshi
authors.forename: Lazaros
authors.initials: L
authors.lastname: Kakalis
authors.forename: Nikita
authors.initials: N
authors.lastname: Matsunaga
authors.forename: Wayne F K
authors.initials: WF
authors.lastname: Schnatter