Unusual Ring-Expansion Reaction of Polyfluorinated Norbornenoxetanes

Autor:	Will J. Marshall, Viacheslav A. Petrov
Rok vydání:	2007
Předmět:	Quenching (fluorescence) Bicyclic molecule Organic Chemistry chemistry.chemical_element Ring (chemistry) n-Butyllithium Medicinal chemistry Catalysis chemistry.chemical_compound chemistry Computational chemistry Reagent Moiety Lithium Methyllithium
Zdroj:	Synthesis. 2007:1349-1354
ISSN:	1437-210X 0039-7881
DOI:	10.1055/s-2007-965999
Popis:	The treatment of norbornenoxetanes (4-halomethyl-4′-trifluoromethyl-3-oxatricyclo[4.2.1.0 2,5 ]non-7-enes) with LDA or RLi reagents results in an unusual ring-expansion reaction leading to the corresponding 2,3-dihydro-4-trifluoromethyl-5-X-furans (X = H, F, Cl, N-C 4 H 9 ). This transformation rapidly proceeds at low temperature and involves intermediate formation of the corresponding ring-opened products, lithium 3-(1,1-dihalo-3,3,3-trifluoroprop-1-en-2-yl)bicyclo[2.2.1]hept-5-en-2-alkoxides, which further undergo intramolecular cyclization to give the corresponding 2,3-dihydro-4-trifluoromethyl-5-X-furans. The corresponding alcohols (X = H, Cl) were isolated after quenching the reaction mixture at low temperature. The ring expansion process provides a simple synthetic procedure for the preparation of fluorinated norbornenes containing 2,3-dihydro-4-trifluoromethylfuran moiety from readily available norbornenoxetanes.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::8aeb358288a8def538759d0fe28cecc2 https://doi.org/10.1055/s-2007-965999 Zobrazit plný text záznamu