Abstract
α-Cyclopropyl-α-trialkylsilyl alkoxides were formed either by addition of cyclopropyllithiums to acylsilanes or by addition of organolithiums to a cyclopropylformylsilane. [1,2]-Brook rearrangement led to α-silyloxy organolithiums which on warming underwent cyclopropane ring opening and [1,5]-retro-Brook rearrangement to yield γ-silyl ketones. Despite the favourability of the cyclopropane ring opening, the Brook rearrangement still required the presence of an anion stabilising group to proceed. β-Silylketones were similarly formed by Brook-retro-Brook rearrangement on warming acylsilanes with a vinyllithium. © 2004 Elsevier Ltd. All rights reserved.
| Original language | English |
|---|---|
| Pages (from-to) | 3195-3203 |
| Number of pages | 8 |
| Journal | Tetrahedron |
| Volume | 61 |
| Issue number | 13 |
| DOIs | |
| Publication status | Published - 28 Mar 2005 |
Keywords
- Anion
- Cyclopropane
- Organolithium
- Rearrrangement
- Silicon