50781-52-7Relevant articles and documents
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
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.
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.