106874-90-2Relevant academic research and scientific papers
PSEUDOESTERS AND DERIVATIVES. XXIII. REACTION OF 3-BROMO-5-METHOXYFURAN-2(5H)-ONE WITH NUCLEOPHILES. FORMATION OF CYCLOPROPANE DERIVATIVES.
Farina, Francisco,Maestro, M. Carmen,Martin, M. Rosario,Martin, M. Victoria,Sanchez, Felix,Soria, M. Luisa
, p. 3715 - 3722 (2007/10/02)
The reactions of 3-bromo-5-methoxyfuran-2(5H)-one (1) with nucleophiles in acetonitrile, in the presence of potassium carbonate and tetrabutylammonium bromide as a catalyst, are reported.The bromofuranone 1 reacts with several carbon and oxygen nucleophiles to give the cyclopropane bis-lactones 7, 8, 11 or 12.When 1 is reacted with diethylamine or propane-2-thiol in a 2:1 ratio, similar cyclopropane bis-lactones 16 or 21, respectively, are formed.This behaviour is explained on the basis of a mechanism involving a double Michael addition, followed by ring closure via internal nucleophilic substitution of the halogen.
