A Novel Tandem [1,2]-Brook/Retro-[1,6]-Brook Rearrangement of a 1-(Trimethylsilyl)-2,4-pentadien-1-ol Anion
β Scribed by Jung, Michael E.; Nichols, Christopher J.
- Book ID
- 121372129
- Publisher
- American Chemical Society
- Year
- 1996
- Tongue
- English
- Weight
- 126 KB
- Volume
- 61
- Category
- Article
- ISSN
- 0022-3263
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π SIMILAR VOLUMES
The retro-[1,4]-Brook rearrangement (also referred to as the West or silyl-Wittig rearrangement) has been employed with acetophenone silyl enol ethers to allow regiospecific migration of the silicon from oxygen to the ortho position of the aromatic ring. The enolate that results from this process ma
At -78Β°C in THF, the tiglyl phenyl sulfide 5 and lithium naphthdenidegave a tiglyl lithium specieswhichunderwentan irreversibleretro-[l,4]-Brookrearrangement givingrise to a 22:78 mixtureof the anti,trans and the syrr,transdinstereomerof the tiglyl silane 6. The same sulfide 5 and potassium naphthal