CYCLOBUTANONE-BASED TANDEM FREE-RADICAL REARRANGEMENTS - FORMATION OFBICYCLIC AND TRICYCLIC KETONES

Authors
DOWD P ZHANG W MAHMOOD K
Citation
P. Dowd et al., CYCLOBUTANONE-BASED TANDEM FREE-RADICAL REARRANGEMENTS - FORMATION OFBICYCLIC AND TRICYCLIC KETONES, Tetrahedron, 51(1), 1995, pp. 39-50
Citations number
45
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
51
Issue
1
Year of publication
1995
Pages
39 - 50
Database
ISI
SICI code
0040-4020(1995)51:1<39:CTFR-F>2.0.ZU;2-T
Abstract
Free radical reaction of endo-bromopropylbicyclo[4.2.0]oct-2-en-7-one 1 leads to deep-seated rearrangement and formation of the bridged tric yclic ketone 2. An authentic sample of 2 was prepared. Reaction of end obromoethylbicyclo[4.2.0]oct-2-en-7-one 18 generates an analogous brid ged tricyclic ketone 20 together with cis-bicyclo[4.4.0]decenone 22. E xperiments using Bu(3)SnD were carried out to explore the mechanism of the transformation leading to 22.