70875-47-7Relevant articles and documents
Reactions of cyclopropanone acetals with alkyl azides: Carbonyl addition versus ring-opening pathways
Grecian, Scott,Desai, Pankaj,Mossman, Craig,Poutsma, Jennifer L.,Aube, Jeffrey
, p. 9439 - 9447 (2007)
(Chemical Equation Presented) The Lewis acid-mediated reactions of substituted cyclopropanone acetals with alkyl azides were found to strongly depend on the structure of the ketone component. When cyclopropanone acetal was treated with alkyl azides, N-substituted 2-azetidinones and ethyl carbamate products were obtained, arising from azide addition to the carbonyl, followed by ring expansion or rearrangement, respectively. When 2,2-dimethylcyclopropanone acetals were reacted with azides in the presence of BF3· OEt2, the products obtained were α-amino-α′- diazomethyl ketones, which arose from C2-C3 bond cleavage of the corresponding cyclopropanone, giving oxyallyl cations that were captured by azides. Aryl-substituted cyclopropanone acetals, when subjected to these conditions, afforded [1,2,3]oxaborazoles exclusively, which were also the result of C2-C3 bond rupture, azide capture, and then loss of nitrogen. In the reactions of n-hexyl-substituted cyclopropanone acetals with alkyl azides, a mixture of 2-azetidinones and regioisomeric [1,2,3]-oxaborazoles was obtained. The reasons for the different behavior of the various systems are discussed.
Preparation of β-lactams from azetidine-2-carboxylic acids and esters
Wasserman,Lipshutz,Tremper,Wu
, p. 2991 - 2999 (2007/10/02)
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