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Trifluoromethyl Isocyanide as a Synthetic Building Block—Reaction with Trifluoroacetic Acid and with Hexafluoroacetone
Author(s) -
Lentz Dieter,
Brüdgam Irene,
Hartl Hans
Publication year - 1987
Publication title -
angewandte chemie international edition in english
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 0570-0833
DOI - 10.1002/anie.198709211
Subject(s) - trifluoroacetic acid , chemistry , isocyanide , imidazole , trifluoromethyl , hexafluoroacetone , block (permutation group theory) , decomposition , medicinal chemistry , organic chemistry , alkyl , geometry , mathematics
N ‐Trifluoromethylformamide 1 and the hexahydropyrrolo[3,4‐ d ]imidazole 2 are the products of the title reaction. 1 is a liquid and can be distilled without decomposition at 116°C; unlike N ‐methylformamide it is preferentially present as the E isomer in non‐polar solvents. The practically quantitative formation of 2 , whose structure could only be elucidated by X‐ray crystallography, is surprising.