NEW FACTS ON THE STEREOSELECTIVITY OF MONOBROMOCARBENOID ADDITIONS TOCYCLIC ALKENES

Authors
DEHMLOW EV LUSTINETZ H
Citation
Ev. Dehmlow et H. Lustinetz, NEW FACTS ON THE STEREOSELECTIVITY OF MONOBROMOCARBENOID ADDITIONS TOCYCLIC ALKENES, Liebigs Annalen, (12), 1996, pp. 2065-2067
Citations number
15
Categorie Soggetti
Chemistry
Journal title
Liebigs Annalen → ACNP
ISSN journal
09473440
Issue
12
Year of publication
1996
Pages
2065 - 2067
Database
ISI
SICI code
0947-3440(1996):12<2065:NFOTSO>2.0.ZU;2-N
Abstract
The monobromocarbenoid derived from CH2Br2 and NaN-(SiMe(3))(2) gives only endo adducts 4, 5, and 6 with 1,5-cyclooctadiene, but shows no se lectivity with 1,3-cyclooctadiene. A literature report of a high endo adduct preference of cyclooctene cannot be duplicated, but cyclodecene is converted to 3 with 100 % selectivity. Bromocarbenoid adducts 11, 13, and 14 of norbornene and norbornadiene are reported. A possible ex planation for the varying selectivities is given.