200066-55-3Relevant articles and documents
Ring expansion by in situ tethering of hydroxy azides to ketones: The boyer reaction
Gracias, Vijaya,Frank, Kristine E.,Milligan, Gregory L.,Aube, Jeffrey
, p. 16241 - 16252 (1997)
Although alkyl azides can react with ketones to form ring- expanded lactams, the reaction suffers from poor generality and the need to use powerful Lewis acid promotion. The reactions of 1,2- and 1,3-hydroxyalkyl azides with ketones yield N-hydroxyalkyl lactams in high yields under the action of protic or Lewis acids such as BF3·OEt2. The reaction appears to succeed due to the initial formation of a hemiketal, which then renders the attack of azide on an oxonium ion intramolecular. The scope of this reaction vis a vis ketone and hydroxyalkyl azide structure is discussed.
