Mechanistic Insight into the Halogen Dance Rearrangement of Iodooxazoles

Autor:	Mathieu F. Chellat, James P. Stambuli, Nicolas Proust
Rok vydání:	2011
Předmět:	Reaction mechanism Dance Organic Chemistry Halide Lithium diisopropylamide Combinatorial chemistry Catalysis chemistry.chemical_compound chemistry Mechanism (philosophy) Halogen dance rearrangement Halogen Organic chemistry
Zdroj:	Synthesis. 2011:3083-3088
ISSN:	1437-210X 0039-7881
DOI:	10.1055/s-0030-1260164
Popis:	The lithium diisopropylamide mediated halogen dance reaction of 5-iodooxazoles to generate 4-iodooxazoles was studied. The mechanism of the reaction was investigated and compared to the reported mechanism for the halogen dance rearrangement of 5-bromooxazoles. Reaction conditions were optimized and yields of iodooxazole were improved to a synthetically useful level. The use of 2-(butylsulfanyl)-5-bromooxazole as an organic catalyst turned out to be the cornerstone for the success of this reaction.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::9d8f1fc3e43e0cc6b8319e0f898905e2 https://doi.org/10.1055/s-0030-1260164 Zobrazit plný text záznamu