TIN(IV) ENOLATES FROM ALLYLIC O-STANNYL KETYLS - REACTIONS WITH ALKYL-HALIDES AND HMPA

Authors
ENHOLM EJ WHITLEY PE
Citation
Ej. Enholm et Pe. Whitley, TIN(IV) ENOLATES FROM ALLYLIC O-STANNYL KETYLS - REACTIONS WITH ALKYL-HALIDES AND HMPA, Tetrahedron letters, 37(5), 1996, pp. 559-562
Citations number
27
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
37
Issue
5
Year of publication
1996
Pages
559 - 562
Database
ISI
SICI code
0040-4039(1996)37:5<559:TEFAOK>2.0.ZU;2-M
Abstract
The mild free radical reaction of an alpha,beta-unsaturated ketone and tributyltin radical produced a resonance-stabilized allylic O-stannyl ketyl intermediate. A subsequent hydrogen atom transfer produced a ti n(IV) enolate which reacts readily with activated alkyl halides and HM PA to provide a useful and mild alternative to analogous Li-NH3 alkyla tions.