ISSN:
1573-9171
Keywords:
ketenimines
;
ketenimine-nitrile rearrangements
Source:
Springer Online Journal Archives 1860-2000
Topics:
Chemistry and Pharmacology
Notes:
Abstract C,C-Substituted N-ethoxyketenimines are extremely unstable even under their generation conditions (dehydrochlorination of N-ethoxyimidoyl chlorides, dehalogenation of α-bromo-N-ethoxyimidoyl halides, the reaction of methylmethoxycarbonylketene with N-ethoxytriphenylphosphinimine) undergo two types of rearrangements: synchronous ring decomposition down to acetaldehyde and the corresponding CH-nitrile and 1,3-migration of the EtO group with formation of α-ethoxynitriles. We suggest that the instability of N-alkoxyketenimines is mainly due to weakening of the NO bond as a result of πCC-σNO* hyperconjugation.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1007/BF00863370
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