Effects of Propargylic Substitution and Annelation on the Cycloaromatization of a Bicyclo[7.3.1] Enediyne
β Scribed by Moss, David K.; Spence, John D.; Nantz, Michael H.
- Book ID
- 126833105
- Publisher
- American Chemical Society
- Year
- 1999
- Tongue
- English
- Weight
- 65 KB
- Volume
- 64
- Category
- Article
- ISSN
- 0022-3263
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π SIMILAR VOLUMES
Although the acetylenic carbon atoms in 2 are closer together than those in 1, only the latter undergoes Bergman cyclization. In contrast, in analogous enediynes without an annelated cyclohexane ring a change in the hybridization of the bridging carbon atom from sp to sp leads to a dramatic increase
## Abstract Bicyclo[7.3.1]diynes 19a and 19b were prepared by using dibromo olefin 11 and ketone 12 as building blocks. The key step of the synthetic sequence is an intramolecular Nicholas reaction of 17 to give the bicyclo[7.3.1]diynβ10βone dicobalthexacarbonyl adducts 18a and 18b (66% total yield