769939-29-9Relevant academic research and scientific papers
Rearrangement of 4-(1-haloalkyl)- and 4-(2-haloalkyl)-2-azetidinones into methyl ω-alkylaminopentenoates via transient aziridines and azetidines
Dejaegher, Yves,De Kimpe, Norbert
, p. 5974 - 5985 (2007/10/03)
The synthesis of 4-(1-haloalkyl)-2-azetidinones and 4-(2-haloalkyl)-2- azetidinones was investigated with use of the Staudinger reaction between in situ generated ketenes and α-haloimines or β-haloimines. This new class of functionalized 2-azetidinones was further evaluated for its potential use as intermediates in the synthesis of highly functionalized compounds. The reaction of 4-(1-haloalkyl)-2-azetidinones and 4-(2-haloalkyl)-2-azetidinones with sodium methoxide in methanol yielded ring-opened products, i.e., methyl 2-alkoxy-4-(alkylamino)pentenoate and methyl 5-(alkyl-amino)pentenoate, respectively. Further attention was paid in detail to the reaction mechanism involved in this peculiar transformation. It was proven that these reactions proceeded via intermediate aziridines or azetidines.
