Regioselective cleavage of the cyclic ethereal bond of 7-oxabicyclo[2.2.1]heptane derivatives mediated by samarium(II) iodide

✍ Scribed by Akihiro Yoshida; Hiroaki Takayama

• Publisher: Elsevier Science
• Year: 2001
• Tongue: French
• Weight: 104 KB
• Volume: 42
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(01)00423-3

✦ Synopsis

It was established that exclusively high regioselective C O bond cleavage of 7-oxabicyclo[2.2.1]heptane skeletons, which are unique Diels-Alder products of furans, under mild conditions using samarium(II) iodide and samarium powder yields cyclohexanol derivatives or aromatic compounds.