50781-52-7Relevant academic research and scientific papers
Rapid and Simple Access to α-(Hetero)arylacetonitriles from Gem-Difluoroalkenes
Hu, Dandan,Liu, Jiayue,Ren, Hongjun,Song, Jinyu,Zhang, Jun-Qi,Zhu, Guorong
supporting information, p. 786 - 790 (2022/01/28)
A scalable cyanation of gem-difluoroalkenes to (hetero)arylacetonitrile derivatives was developed. This strategy features mild reaction conditions, excellent yields, wide substrate scope, and broad functional group tolerance. Significantly, in this reacti
Synthesis of 9-fluorenylidenes and 9,10-phenanthrenes through palladium-catalyzed aryne annulation by o-halostyrenes and o-halo allylic benzenes
Worlikar, Shilpa A.,Larock, Richard C.
supporting information; experimental part, p. 9132 - 9139 (2010/03/01)
(Chemical Equation Presented) A number of functionally substituted 9-fluorenylidenes and 9,10-phenanthrenes have been synthesized from substituted o-halostyrenes and o-halo allylic benzenes respectively in good yields by the palladium-catalyzed annulation
Investigation of the reaction of 2-bromo-1,4-dimethoxynaphthalene and 9-bromophenanthrene with nitriles under aryne-forming conditions
Hansen,Khanapure,Fry,Swartling,Biehl
, p. 957 - 960 (2007/10/02)
The reaction of 2-bromo-1,4-dimethoxynaphthalene (1) and 9-bromophenanthrene (3) with nitriles 2 under base-mediated, aryne-forming conditions gives product distributions which depend upon the nature of the bromoarene, nitrile, base, and the reaction medium. Thus, treatment of 1 with arylacetonitriles 2a-d in the presence of LDA in THF or sodium amide in liquid ammonia supplies α-aryl-1,4-dimethoxy-2-naphthylacetonitriles 4a-d, presumably by the aryne arylation mechanism. In contrast, the reaction of 9-bromophenanthrene (3) and arylacetonitriles 2b-e with LDA in THF yields 10-arylmethyl-9-phenanthrenecarbonitriles 6b-e, most likely by the tandem addition-rearrangement pathway. When 3 reacts with 2a-c in the presence of sodium amide and liquid ammonia, α-aryl-9-phenanthrylacetonitriles 5a-c, rather than the rearranged nitriles 6a-c, are obtained. Both 1 and 3 react with alkylnitriles 2f-i and LDA-THF, sodium amide-liquid ammonia, or Caubere's sodamide base to afford aryne arylated nitriles (4f-i and 5f-i, respectively). An explanation in terms of the influence of reactants and solvent on the competition between the aryne arylation and tandem addition-rearrangement pathways is presented.
Synthesis and spectroscopy of nine isomeric methylacephenanthrylenes
Mulder, Patrick P. J.,Boere, Ben B.,Baart, Arthur,Cornelisse, Jan,Lugtenburg, Johan
, p. 22 - 32 (2007/10/02)
The synthesis of nine isomeric methyl-substituted acephenanthrylenes is described.Three different approaches were used. 1-, 2-, And 6-methylacephenanthrylene (1a, 1c and 1f) were prepared by formylation of acephenanthrene (2) and 4,5,7,8,9,10-hexahydroacephenanthrylene (17), followed by Wolff-Kishner reduction and dehydrogenation. 4-, 5-, 7- And 10-methylacephenanthrylene (1d, 1e, 1g and 1j) were synthesized by treating the corresponding acephenanthrenones with methyllithium, followed by dehydration and, in the case of 1g and 1j, dehydrogenation. 8- And 9-methylacephenanthrylene (1h and 1i) were prepared by a Haworth synthesis starting with the reaction of methylsuccinic anhydride with acenaphthene. the spectroscopic properties of acephenanthrylene and its methyl derivatives were investigated with mass spectrometry, (1)H NMR and UV-VIS spectroscopy.According to the (1)H NMR spectra, steric hindrance between the methyl group and nearby protons decreases in the following order: 1, 10 > 6 > 7 > 3 > 4, 5, 8, 9.
A Useful Access to 9-Phenanthrylmethyl Derivatives
Fernandez, Franco,Gomez, Generosa,Lopez, Carmen,Santos, Ana
, p. 802 - 803 (2007/10/02)
Chloromethylation of phenanthrene to give 9-chloromethylphenanthrene and conversions of this compound into other 9-phenanthrylmethyl derivatives in useful yields are described.
