ISOMERIZATION OF 2-(2-PROPENOXY)PHENYLLITHIUM - TANDEM ANIONIC CYCLIZATION GAMMA-ELIMINATION

Authors
BAILEY WF PUNZALAN ER
Citation
Wf. Bailey et Er. Punzalan, ISOMERIZATION OF 2-(2-PROPENOXY)PHENYLLITHIUM - TANDEM ANIONIC CYCLIZATION GAMMA-ELIMINATION, Tetrahedron letters, 37(31), 1996, pp. 5435-5436
Citations number
10
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
37
Issue
31
Year of publication
1996
Pages
5435 - 5436
Database
ISI
SICI code
0040-4039(1996)37:31<5435:IO2-TA>2.0.ZU;2-U
Abstract
2-(2-Propenoxy)phenyllithium (1), which may be prepared from the corre sponding iodide by low-temperature lithium-iodine exchange, rearranges on warming in the presence of TMEDA via 5-exo cyclization to (2,3-dih ydrobenzofuranyl)methyllithium (2) followed by gamma-elimination to gi ve variable amounts of the lithium salt of 2-(cyclopropyl)phenol (3). Copyright (C) 1996 Elsevier Science Ltd