Relative kinetic ordering of [1,3]-hydrogen migration, anionic oxy-cope rearrangement, and base-accelerated dehydration in tertiary cyclononatrienyl alkoxides
✍ Scribed by Gary D. Crouse; Leo A. Paquette
- Book ID
- 104234186
- Publisher
- Elsevier Science
- Year
- 1981
- Tongue
- French
- Weight
- 264 KB
- Volume
- 22
- Category
- Article
- ISSN
- 0040-4039
No coin nor oath required. For personal study only.
✦ Synopsis
The reactivity exhibited by l-methyl-and l-ethyl-cis3 -2,4,7-cyclononatrienol toward -KH under various conditions has been examined. Recent research activities have demonstrated that a highly ionized alkoxide substituent can substantially accelerate oxy-Cope rearrangements,i [1,51-dienyl hydrogen shifts,2 [1,33-? and [4+2] cycloreversions. 4 sigmatropic carbon migrations, At least where oxy-Cope rearrangements are concerned, excellent stereochemical control can be achieved, and stereoselective syntheses based on this principle have been described for (+)-juvabione,i the primary prostaglandins,2 various germacrane sesquiterpenes, 5 and (&)-coronafacic acid.6 Pivotal to our earlier