92548-75-9Relevant academic research and scientific papers
Vinyl aryl ethers from copper-catalyzed coupling of vinyl halides and phenols
Wan, Zhonghui,Jones, Chauncey D.,Koenig, Thomas M.,Pu, Y. John,Mitchell, David
, p. 8257 - 8259 (2007/10/03)
A general procedure for vinyl aryl ether bond formation by direct coupling of vinyl halides and phenols under mild Ullmann-type reaction conditions has been developed. Using copper chloride as the catalyst and cesium carbonate as the base, vinyl bromides or iodides were reacted with phenols in refluxing toluene to produce vinyl aryl ethers in good to excellent yields.
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.
