Electronic Resource
Weinheim
:
Wiley-Blackwell
Angewandte Chemie International Edition in English
7 (1968), S. 25-36
ISSN:
0570-0833
Keywords:
Lactams
;
Aziridinones
;
Chemistry
;
General Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
α-Lactams have often been postulated as intermediates in numerous processes. The isolation of the first α-lactam, N-tert-butyl-3-phenylaziridinone, was accomplished in 1962. Since then, further N- and C-3-substituted α-lactams have been synthesized. Most of these very reactive compounds undergo easy thermal decomposition; remarkable is the relative stability of 1,3-di-tert-butylaziridinone, which does not start to decompose below 140°C. The α-lactam ring is opened by nucleophilic reagents. - The correlation of stability and substituents is discussed in the last section. An acyclic, planar or almost planar, charge-delocalized intermediate is suggested to explain the observed effects.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/anie.196800251
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