The synthesis and structure of 10,11-bistrifluoromethyl-i,o-bicyclo[7.2.2]trideca-10,12-diene. A highly strained inside-outside bicycloalkane derivative.
✍ Scribed by Paul G. Gassman; Stewart R. Korn; Thomas F. Bailey; Thomas H. Johnson; Janet Finer; Jon Clardy
- Book ID
- 104246417
- Publisher
- Elsevier Science
- Year
- 1979
- Tongue
- French
- Weight
- 244 KB
- Volume
- 20
- Category
- Article
- ISSN
- 0040-4039
No coin nor oath required. For personal study only.
✦ Synopsis
l0,11-Bistrifluoromethyl-i,o-bicyclo[7.2.2]trideca-lO,l2-diene has been prepared by the Diels-Alder addition of hexafluoro-2-butyne to cis, trans-cycloundeca-1,3-diene. Purification was accomplished via formation of an iron tricarbonyl complex whose structure was established via X-ray crystallography. Relatively little is known about the chemistry of inside-outside bicyclic molecules. Of the few known examples3-5 of such carbocyclic systems, only thei,o-bicyclo[8.2.2]tetradeca-11, 13-diene derivatives showed behavior which could be associated with ring strain.4-6 Because of the somewhat unusual chemical reactivity of 1, we were intrigued with the possibility of preparing even more highly strained molecules with inverted bridgeheads. We now wish to report the synthesis of 10,