Isomerization of 2-(2-propenoxy)phenyllithium: Tandem anionic cyclization-γ-elimination

Article abstract of DOI:10.1016/0040-4039(96)01142-2

2-(2-Propenoxy)phenyllithium (1), which may be prepared from the corresponding iodide by low-temperature lithium-iodine exchange, rearranges on warming in the presence of TMEDA via 5-exo cyclization to (2,3-dihydrobenzofuranyl)methyllithium (2) followed by γ-elimination to give variable amounts of the lithium salt of 2-(cyclopropyl)phenol (3).