RADICAL-INDUCED EPOXIDE FRAGMENTATION CHEMISTRY - N-BU3SN RADICAL CATALYZED ISOMERIZATION OF EPOXYKETONES TO CARBOCYCLES

Authors
RAWAL VH KRISHNAMURTHY V FABRE A
Citation
Vh. Rawal et al., RADICAL-INDUCED EPOXIDE FRAGMENTATION CHEMISTRY - N-BU3SN RADICAL CATALYZED ISOMERIZATION OF EPOXYKETONES TO CARBOCYCLES, Tetrahedron letters, 34(18), 1993, pp. 2899-2902
Citations number
25
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
34
Issue
18
Year of publication
1993
Pages
2899 - 2902
Database
ISI
SICI code
0040-4039(1993)34:18<2899:REFC-N>2.0.ZU;2-3
Abstract
Cyclic alpha,beta-epoxyketones are converted to bi- or tricyclic beta- hydroxyketones in the presence of n-Bu3Sn. radical. Addition of n-Bu3S n. to the carbonyl group gives a ketyl radical that triggers the epoxi de fragmentation which is then followed by a 1,5-hydrogen abstraction and cyclization. Reversibility in the last two steps of the sequence i s demonstrated.