Synthesis of tetrahydrofurans by a tandem hydrogen atom abstraction/radical nucleophilic displacement sequence

Authors
Crich, D Huang, XH Newcomb, M
Citation
D. Crich et al., Synthesis of tetrahydrofurans by a tandem hydrogen atom abstraction/radical nucleophilic displacement sequence, ORG LETT, 1(2), 1999, pp. 225-227
Citations number
16
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
ORGANIC LETTERS
ISSN journal
15237060 → ACNP
Volume
1
Issue
2
Year of publication
1999
Pages
225 - 227
Database
ISI
SICI code
1523-7060(19990729)1:2<225:SOTBAT>2.0.ZU;2-P
Abstract
The reaction of a series of 5-(N-phthalimidoxy)-1-phenyl-1-(diphenylphospha toxy)pentanes with triphenyltin hydride and AIBN provides alkoxy radicals w hich undergo 1,5-hydrogen atom abstraction to give beta-(phosphatoxy)alkyl radicals. These radicals then take part in a radical nucleophilic displacem ent leading, after chain transfer, to tetrahydrofurans.