ChemInform Abstract: Ring Expansion by in situ Tethering of Hydroxy Azides to Ketones: The Boyer Reaction

Autor:	Vijaya Gracias, Kristine E. Frank, Jeffrey Aubé, Gregory L. Milligan
Rok vydání:	2010
Předmět:	chemistry.chemical_classification chemistry.chemical_compound Ketone Chemistry Intramolecular force Yield (chemistry) General Medicine Lewis acids and bases Azide Ring (chemistry) Oxonium ion Medicinal chemistry Alkyl
Zdroj:	ChemInform. 29
ISSN:	1522-2667 0931-7597
DOI:	10.1002/chin.199811185
Popis:	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 BF 3 ·OEt 2 . 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.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::715916ef6fea27f266454d61b4d1c1e9 https://doi.org/10.1002/chin.199811185 Zobrazit plný text záznamu Plný text