77408-43-6Relevant academic research and scientific papers
Convenient Synthesis of Biphenyl-2-carboxylic Acids via the Nucleophilic Aromatic Substitution Reaction of 2-Methoxybenzoates by Aryl Grignard Reagents
Hattori, Tetsutaro,Suzuki, Takatsugu,Hayashizaka, Noriyuki,Koike, Nobuyuki,Miyano, Sotaro
, p. 3034 - 3040 (2007/10/02)
Nucleophilic aromatic substitution (SNAr) of 2-methoxybenzoic esters derived from 2,6-dialkylphenols by aryl Grignard reagents affords 1,1'-biphenyl-2-carboxylates in excellent yields by proper choice of the bulk of the 2,6-dialkyl-substituents. The phenoxyl protecting groups can be easily removed from the resulting biphenyl-2-carboxylates to the free acids by treatment with potassium hydroxide in aqueous ethanol (2,4,6-trimethylphenyl and 2,6-diisopropylphenyl esters) or sodium methoxide in toluene-hexamethylphosphoric triamide (2,6-di-t-butyl-4-methylphenyl esters). The regioselective biphenyl coupling reaction via the SNAr process is utilized for the key-step construction of the biphenyl skeleton in a formal synthesis of cannabinol.
Synthesis of S-Substituted Benzils and Some Hindered Biphenyls
Luedersdorf, Reinhard,Mai, Juergen,Praefcke, Klaus
, p. 1420 - 1425 (2007/10/02)
Three methylthio and/or methylsulfinyl substituted benzils (2, 6 and 7) have been synthesized on photo- or thermochemical routes, respectively.Photodecarboxylation of some new different substituted mesityl benzoates (1a-e) leads to hindered biphenyls (3a-e) accompanied sometimes by aldehyde (4a-c) and benzil formation (2) due to compatitive α-cleavage and subsequent stabilization processes of such generated free aroyl radicals.A short summary on constitutional conditions for intramolecular photoredox reactions of ortho functionalized aryl sulfinyl compounds is presented. - Keywords: Photodecarboxylations, α-Cleavages, Photoredox Reactions, Sulfoxides
