UNPRECEDENTED FORMATION OF SPIROBICYCLO[3.1.0]HEXANES THROUGH TANDEM ACETYLENE-ADDITION - MICHAEL CYCLIZATION

Authors
BROESS AIA GROEN MB HAMERSMA H
Citation
Aia. Broess et al., UNPRECEDENTED FORMATION OF SPIROBICYCLO[3.1.0]HEXANES THROUGH TANDEM ACETYLENE-ADDITION - MICHAEL CYCLIZATION, Tetrahedron letters, 35(2), 1994, pp. 335-338
Citations number
10
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
35
Issue
2
Year of publication
1994
Pages
335 - 338
Database
ISI
SICI code
0040-4039(1994)35:2<335:UFOSTT>2.0.ZU;2-K
Abstract
Reaction of 4-pentynyltriphenylphosphonium bromide 2 with oestrone met hyl ether in the presence of potassium tert-butylate produced a spirob icyclo[3.1.0]hexane rather than the anticipated Wittig product. The re action appears to be general for pinacolone-type ketones, as was demon strated by several examples. A mechanism for this anomalous reaction i s proposed.