title: Intramolecular aromatic 1,5-hydrogen transfer in free radical reactions III. Reactivity of diaryl ketones, ethers, thioethers, sulfoxydes, and sulfones. An experimental and theoretical study.
abstract: [reaction: see text] Experiments show that free radical hydrogen shift is significant in the Pschorr cyclization of diphenyl ethers (X = O) and thioethers (X = S) and does not take place with sufoxides (X = SO) and sulfones (X = SO(2)). DFT calculations of the product ratios, activation energies, rate constants for H-transfers, and ring-closings at the UB3PW91/6-31G(d,p) level are in excellent agreement with the experimental results reported here and elsewhere in the literature.
authors.affiliation: Process Research Department, Merck Research Laboratories, Merck and Company, P.O. Box 2000, Rahway, New Jersey 07065, USA. sandor_karady@merck.com
authors.forename: Sandor
authors.initials: S
authors.lastname: Karady
authors.forename: Jordan M
authors.initials: JM
authors.lastname: Cummins
authors.forename: J J
authors.initials: JJ
authors.lastname: Dannenberg
authors.forename: Emma
authors.initials: E
authors.lastname: del Rio
authors.forename: Peter G
authors.initials: PG
authors.lastname: Dormer
authors.forename: Benjamin F
authors.initials: BF
authors.lastname: Marcune
authors.forename: Robert A
authors.initials: RA
authors.lastname: Reamer
authors.forename: Tomas L
authors.initials: TL
authors.lastname: Sordo