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Reaction of 1‐oxa‐3‐azabutatrienium salts with tertiary carboxamides
Author(s) -
AlTalib Mahmoud,
Jibril Ibrahim,
Huttner Gottfried,
Jochims Johannes C.
Publication year - 1985
Publication title -
chemische berichte
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.667
H-Index - 136
eISSN - 1099-0682
pISSN - 0009-2940
DOI - 10.1002/cber.19851180513
Subject(s) - chemistry , electrophile , lewis acids and bases , moiety , medicinal chemistry , stereochemistry , catalysis , organic chemistry
α‐Chloro isocyanates 1 react with tertiary carboxamides or acylimines 3 in the presence of Lewis acids (SbCl 5 , FeCl 3 ) to give the amino‐substituted 2‐azaallenium salts 5a – t under mild conditions. With methanol the moderately strong electrophiles 5 afford the acetals 8 and 10 . According to an X ‐ray structural analysis, the C N C unit of 5a is bent by 128°. There exists a linear relationship between the wave number of the antisymmetric stretching vibration of 2‐azaallenium salts and the bond angle. The planes defined by the sp 2 carbons of the moiety of 5a are almost perpendicular (84°) with respect to each other.