How 2-anilinovinyl perfluoroalkyl ketones can be mechanistically correlated with their cyclization products 2-(perfluoroalkyl)quinolines

When heated in the presence of phosphoryl chloride, 2-anilinovinyl perfluoroalkyl ketones [e.g., 4-anilino-1,1,1-trifluoro-3-buten-2-one] gave 2-(perfluoroalkyl)quinolines [e.g., 2-(trifluoromethyl)quinoline]. As revealed by cross-over expts., an efficient amine exchange process randomizes the structural component in the final products but not in their aminoenone precursors. 1,3-Diaminoallyl cations (vinylogous formidinium salts) are postulated to act as the turntables. [on SciFinder (R)]


Published in:
Tetrahedron Letters, 38, 49, 8523-8526
Year:
1997
Keywords:
Note:
CAN 128:75286
27-17
Heterocyclic Compounds (One Hetero Atom)
Institut de Chimie Organique de l'Universite Batiment de Chimie (BCh),Lausanne-Dorigny,Switz.
Journal
0040-4039
written in English.
2787-31-7; 176722-51-3 (1,1,1-Trifluoro-4-(phenylamino)-3-buten-2-one) Role: RCT (Reactant), RACT (Reactant or reagent) (cyclization of fluoro(phenylamino)alkenones); 13122-28-6P (Benzen-4-d-amine); 200617-28-3P; 200617-29-4P; 200617-30-7P; 200617-31-8P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (cyclization of fluoro(phenylamino)alkenones); 347-42-2P; 57702-79-1P; 200617-32-9P; 200617-33-0P; 200617-34-1P; 200617-35-2P; 200617-36-3P; 200617-37-4P; 200617-38-5P; 200617-39-6P; 200617-40-9P; 200617-41-0P Role: SPN (Synthetic preparation), PREP (Preparation) (prepn. of)
Laboratories:




 Record created 2006-03-03, last modified 2018-01-27


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