AN UNUSUAL RADICAL FRAGMENTATION OF 8A-CYCLOALKENYLMETHYL WIELAND-MIESCHER KETONES MEDIATED BY TRI-N-BUTYLTIN HYDRIDE

Authors
RAJAMANNAR T BALASUBRAMANIAN KK
Citation
T. Rajamannar et Kk. Balasubramanian, AN UNUSUAL RADICAL FRAGMENTATION OF 8A-CYCLOALKENYLMETHYL WIELAND-MIESCHER KETONES MEDIATED BY TRI-N-BUTYLTIN HYDRIDE, Tetrahedron letters, 35(4), 1994, pp. 637-640
Citations number
20
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
35
Issue
4
Year of publication
1994
Pages
637 - 640
Database
ISI
SICI code
0040-4039(1994)35:4<637:AURFO8>2.0.ZU;2-I
Abstract
The behaviour of tri-n-butyltin hydride in poly functional molecule Li ke Wieland-Miescher ketones, was found to be very unusual, a remarkabl e difference in chemoselectivity was noticed in the reductive cyclisat ion of cycloalkenyl bromides, resulting in the remote generation of th e bromocyclopentenyl-methyl radical by a homolytic C-C bond cleavage.