SEQUENTIAL HYDROSTANNYLATION-CYCLIZATION OF DELTA-ALLENYL AND OMEGA-ALLENYL ARYL HALIDES - CYCLIZATION AT THE PROXIMAL CARBON

Authors
GRIGG R SANSANO JM
Citation
R. Grigg et Jm. Sansano, SEQUENTIAL HYDROSTANNYLATION-CYCLIZATION OF DELTA-ALLENYL AND OMEGA-ALLENYL ARYL HALIDES - CYCLIZATION AT THE PROXIMAL CARBON, Tetrahedron, 52(42), 1996, pp. 13441-13454
Citations number
31
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
52
Issue
42
Year of publication
1996
Pages
13441 - 13454
Database
ISI
SICI code
0040-4020(1996)52:42<13441:SHODAO>2.0.ZU;2-M
Abstract
Palladium catalysed hydrostannylation of (Bu(3)SnH, THF, degrees C) of delta- and omega-allenyl aryl halides followed by mono- or bis-cyclis ation (MeCN, 80 degrees C) affords small (5-7), large (11-17) and spir ocyclic rings in which cyclisation occurs at the proximal carbon of th e original allene. The reaction proceeds via stereoselective allylstan nane formation. The cyclisation products are alpha-vinyl oxygen- and n itrogen-heterocycles. Copyright (C) 1996 Elsevier Science Ltd