ISSN:
0009-2940
Keywords:
Ketenimines, N-silyl- and N-acyl-
;
Nitrile anions
;
α-Cyano ketones
;
Regiochemistry of acylation reactions
;
Calculations, MNDO
;
Chemistry
;
Inorganic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
Acylation of N-(Trimethylsfly1)ketenimines: N-Acylketenimines and α-Cyano KetonesThe acylation reactions of N-(trimethylsilyl)ketenimines 1 with different acyl halides 4 yields N-acylketenimines 2 and/or α-cyano ketones 3, depending on the substitution pattern of compounds 1 and the halogen atom in 4. In some cases, novel adducts of enamide type 5, 6 are isolated. The new N-acylketenimines 2a, b are stable at room temperature and have been fully characterized; compounds 2c, d, however, were found to dimerize yielding the 1,3,5-oxadiazines 7. For comparison, the analogous acylation reactions of nitrile anions were also studied. MNDO calculations are used to rationalize the regiochemistry in terms of kinetic and thermodynamic control.
Additional Material:
2 Tab.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/cber.19901231218
