622. Aromatic polyfluoro-compounds. Part XI. Pentafluoro-phenyl-lithium and derived compounds

Abstract

Coe, Stephens, and Tatlow. 3227 622. Aromatic PolyJluoro-compounds. Part XI.* PentaJluorophenyl-lithium and Derived Compounds.

Fluoronaphthalene Building Blocks via Arynes: A Solution to the Problem of Positional Selectivity

“…Under such conditions, 1,4-epoxy-1,4-dihydro-5,6,7,8-tetrafluoronaphthalene was smoothly isomerized to afford 5,6,7,8-tetrafluoro-1-naphthol in 70 % [22] and 93 % yield. [23] The silyl-substituted cycloadduct 2 was found to undergo 1,4-epoxide opening 0.12 times as fast as the unsubstituted parent compound.…”

Pentafluorobenzaldehyde and its utilizing in organic synthesis

“…After the nucleophilic addition of the amino group, a temporary cyclization of the thiole group on the aldehydic group occurs, yielding 43% of 2-dihydrobenzthiazolylpentafluorobenzene and 21% of 2-benzthiazolyl-pentafluorobenzene (Scheme 49). The similar synthesis of 2-(2,3,4,5,6-pentafluorophenyl)-1,4-dihydro-2H-benzo[d] [1,3]oxazine and 2-(2,3,4,5,6-pentafluorophenyl)-1,4-dihydro-2H-benzo[d] [1,3]thiazolidine from the 2-aminobenzylalcohol, o-aminobenzenethiole and the PFBA is shown below (Scheme 49 [566,567]). …”

“…Another synthesis of pentafluorobenzaldehyde was based on preparation of organolithium compound 4 from bromopentafluorobenzene [3]. Preparation of 4 was realized by two ways: the first involving substitution of bromine by lithium with n-BuLi and the second being the direct metallation with lithium amalgam-a mixture of lithium and mercury.…”

The Kinetic Acidity of Oligofluorobenzenes Correlated with Their Gas Phase Deprotonation Energies

“…105-106 8C) are well documented in the literature as are their methyl esters. 2-Chloro-1,3-trifluorobenzene, [24] 2-chloro-1,4-difluorobenzene, [25] 2-chloro-1,3,4-trifluorobenzene, [26] 3-chloro-1,2,4,5-tetrafluorobenzene, [27] and chloropentafluorobenzene [28] are also known compounds. Transmetalation experiments: 1,3-Difluorobenzene (1.0 mL, 1.1 g, 10 mmol) was mixed with a solution of sec-butyllithium (10 mmol) in tetrahydrofuran (14 mL) and hexanes (6 mL) cooled in a dry ice/methanol bath.…”