AN EFFECTIVE REGIOSELECTIVE ELECTROPHILIC HALOGENATION OF TRICYCLO[5.2.1.0(2,6)]DECENYL ENAMINONES

Authors
RAMESH NG HEIJNE EH KLUNDER AJH ZWANENBURG B
Citation
Ng. Ramesh et al., AN EFFECTIVE REGIOSELECTIVE ELECTROPHILIC HALOGENATION OF TRICYCLO[5.2.1.0(2,6)]DECENYL ENAMINONES, Tetrahedron letters, 39(20), 1998, pp. 3295-3298
Citations number
18
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
39
Issue
20
Year of publication
1998
Pages
3295 - 3298
Database
ISI
SICI code
0040-4039(1998)39:20<3295:AEREHO>2.0.ZU;2-S
Abstract
no-endo-tricyclo[5.2.1.0(2,6)]deca-4,8-dien-3-ones 4 undergo a surpris ingly effective regioselective halogenation using N-halosuccinimides ( NXS) under electrophilic conditions. Exclusive alpha-halogenation is o bserved using one equiv. of NXS, whereas, either alpha,gamma- or alpha ,N-bishalogenation products are formed in quantitative yields when an additional equiv. of NXS is applied. Most importantly, halogenation of the C-8-C-9 norbornene bond is not observed (C) 1998 Elsevier Science Ltd. All rights reserved.