Inter- and intramolecular palladium-catalyzed hydrocarbonation of methylenecyclopropanes with carbon pronucleophiles

Authors
Tsukada, N Shibuya, A Nakamura, I Kitahara, H Yamamoto, Y
Citation
N. Tsukada et al., Inter- and intramolecular palladium-catalyzed hydrocarbonation of methylenecyclopropanes with carbon pronucleophiles, TETRAHEDRON, 55(29), 1999, pp. 8833-8844
Citations number
45
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON
ISSN journal
00404020 → ACNP
Volume
55
Issue
29
Year of publication
1999
Pages
8833 - 8844
Database
ISI
SICI code
0040-4020(19990716)55:29<8833:IAIPHO>2.0.ZU;2-L
Abstract
The inter- and intramolecular additions of pronucleophiles to methylenecycl opropanes proceeded smoothly in the presence of catalytic amounts of Pd(PPh 3)(4), affording hydrocarbonation products in good to high yields. The ring opening of methylenecyclopropanes mainly occurred at the distal position t o the exomethylene. In some cases, proximal bond cleavage also took place. The mode of ring opening depended upon both the structure of the pronucleop hile and the substituent at the exomethylene carbon. (C) 1999 Elsevier Scie nce Ltd. AII rights reserved.