57076-47-8Relevant academic research and scientific papers
From insertion to multicomponent coupling: Temperature dependent reactions of arynes with aliphatic alcohols
Thangaraj, Manikandan,Bhojgude, Sachin Suresh,Mane, Manoj V.,Biju, Akkattu T.
supporting information, p. 1665 - 1668 (2016/01/30)
The temperature dependent selectivity switch in the reaction of arynes with aliphatic alcohols in THF has been reported. At -20°C, arynes smoothly insert into the O-H bond of alcohols to form alkyl aryl ethers. Interestingly, at 60°C, a highly selective multicomponent coupling occurs with the solvent THF acting as the nucleophilic trigger affording (4-(alkoxy)butoxy)arenes.
Benzyl protection of phenols under neutral conditions: Palladium-catalyzed benzylations of phenols
Kuwano, Ryoichi,Kusano, Hiroki
supporting information; experimental part, p. 1979 - 1982 (2009/04/10)
Benzyl protection of phenols under neutral conditions was achieved by using a Pd(n3-C3H5)Cp-DPEphos catalyst. The palladium catalyst efficiently converted aryl benzyl carbonates into benzyl-protected phenols through the decarboxylative etherification. Alternatively, the nucleophilic substitution of benzyl methyl carbonates with phenols proceeded In the presence of the catalyst, yielding aryl benzyl ethers.
Reactivity of functionalized arylcarbenes. 2-Phenylethyl side chains and hetero analogues
Kirmse, Wolfgang,Konrad, Wolfgang,Oezkir, Ismail S.
, p. 9935 - 9964 (2007/10/03)
Phenylcarbenes with -X-CH2Ph and -CH2-X-Ph (X = CH2, O, SiMe2) groups in the ortho position were generated thermally and photolytically from diazo or tosylhydrazone precursors. Stereorandom insertion reactions with β-C-H bonds were observed, pointing to a triplet abstraction-recombination mechanism. Large kinetic and stereochemical deuterium isotope effects support this notion. The ample formation of benzocyclobutenes from 2-CH2-X-Ph substrates is due to insertion of the carbenes into ArCH2-X bonds. Addition to the terminal phenyl groups competes with C-H and C-X insertion. The results of benzophenone sensitization and of trapping with methanol suggest that the intramolecular reactions of functionalized arylcarbenes proceed, at best, competitively with spin inversion.
