21567-19-1Relevant academic research and scientific papers
Metal-free oxidative aromatization of 2-aryloxycyclohex-2-en-1-ones to 2-aryloxyphenols using DDQ/Amberlyst-15
Jadhav,Samant
, p. 1301 - 1305 (2015/01/08)
Efficient metal-free oxidative aromatization of 2-aryloxycyclohex-2-en-1-ones was achieved by a combination of 2,3-dichloro-5,6-dicyano-p-benzoquinone (DDQ) and Amberlyst-15. The conditions for oxidative aromatization are mild and applicable for a variety of substrates, and Amberlyst-15 can be successfully recovered and recycled.
Syntheses of dibenzodioxin derivatives via iron complexes, and further functionalizations via directed metallation
Cambie, Richard C.,Janssen, Sally J.,Rutledge, Peter S.,Woodgate, Paul D.
, p. 387 - 418 (2007/10/02)
Double nucleophilic aromatic substitution reactions between (cyclopentadienyl)(η6-1,2-dichlorobenzene)iron(1 +) salts and substituted 1,2-benzenediols have been carried out under mild conditions to prepare 6-dibenzodioxin>iron(1 +) complexes functionalized in the 1- or 2-position with an alkyl, aldehyde, carboxylic acid, methoxycarbonyl, carboxamide, or hydroxy group. 3-Methyl- and 4-methyl-(η6-1,2-dichlorobenzene)iron complexes were treated with substituted 1,2-benzenediols to effect functionalization of both aromatic rings of the heterocycle.The dibenzodioxin ligands were liberated routinely by irradiation with ultraviolet light.Directed deprotonation of the free functionalized dibenzodioxins with an alkyllithium reagent followed by quenching with a variety of electrophiles yielded further derivatives, including two new isoindolone systems.
ARENE COMPLEXES OF TRANSITION METALS IN REACTIONS WITH NUCLEOPHILIC REAGENTS. XI. SYNTHESIS OF HETEROCYCLIC COMPOUNDS BY NUCLEOPHILIC SUBSTITUTION OF CHLORINE ATOMS IN η6-o-DICHLOROBENZENECHROMIUM TRICARBONYL
Litvak, V. V.,Goryunov, L. I.,Shteingarts, V. D.
, p. 138 - 144 (2007/10/02)
A method was developed for the synthesis of dibenzo-1,4-dioxin, phenoxazine, and phenoxathiin and also their chromium tricarbonyl complexes by the reaction of η6-o-dichlorobenzenechromium tricarbonyl with the alkali-metal salts of pyrocatechol, o-aminophenol, and o-mercaptophenol in HMPTA.The composition of the reaction products and the yield of the heterocyclic compounds depend significantly on the nature of the solvent, the nucleophile, the condensing agent, and the reaction conditions.
Cyclodienones. X. Reaction of Halo-cyclohexadien-1-ones with Phenols in the Presence of α-Picoline and Preparation of 4-Hydroxy- and 2-Hydroxyphenyl Aryl Ethers
Tashiro, Masashi,Itoh, Takashi,Fukata, Gouki
, p. 416 - 420 (2007/10/02)
Reaction of 4-halocyclohexadienones such as 4-bromo-(1a), 4-chloro-2,4,6-tri-t-butyl-(1b), 2,4-dichloro-4,6-di-t-butyl-2,5-cyclohexadien-1-one, and 2,4-dichloro-2,6-di-t-butyl-3,5-cyclohexadien-1-one with phenols in the presence of α-picoline was carried out under various conditions.The reaction of 1a and 1b with phenols afforded the corresponding 2-aryloxy-4,6-di-t-butyl phenols together with various by-products.The AlCl3 catalyzed trans-t-butylation of 2-aroxy-4,6-di-t-butyl-phenols, which were obtained by the above reaction, afforded the corresponding 2-hydroxyphenyl aryl ethers.The similar reaction of 4-aroxy-2,4,6-tri-t-butyl-2,5-cyclohexadien-1-ones also afforded the corresponding 4-hydroxyphenyl aryl ethers.
