Metalation of Olefinic Positions in Norbornadiene: Enhancement and Attenuation of Kinetic CH-Acidities by a Neighboring Enesilane Moiety
When treated with butyllithium in the presence of sodium or potassium tert-butoxide, 2-trimethylsilyl- and 2-triethylsilyl-norbornadiene undergo hydrogen/metal-exchange mainly at the 5-position. The latter position is found to be slightly activated relative to unsubstituted norbornadiene while the...
Saved in:
| Main Authors: | , |
|---|---|
| Format: | Article |
| Language: | deu |
| Published: |
Swiss Chemical Society
1986-09-01
|
| Series: | CHIMIA |
| Online Access: | https://www.chimia.ch/chimia/article/view/9746 |
| Tags: |
Add Tag
No Tags, Be the first to tag this record!
|
| Summary: | When treated with butyllithium in the presence of sodium or potassium tert-butoxide, 2-trimethylsilyl- and 2-triethylsilyl-norbornadiene undergo hydrogen/metal-exchange mainly at the 5-position. The latter position is found to be slightly activated relative to unsubstituted norbornadiene while the two other olefinic positions prove to be quite inert. Two side reactions are observed: the metalation of silicon-attached methyl groups and the replacement of the entire trialkylsilyl group by a metal atom.
|
|---|---|
| ISSN: | 0009-4293 2673-2424 |