Protonation of the isopropenylcyclopentadienyl anion : trapping of the isomer mixture with tetracyanoethylene
- UNCG Author/Contributor (non-UNCG co-authors, if there are any, appear on document)
- Ray Lawson Hartless (Creator)
- Institution
- The University of North Carolina at Greensboro (UNCG )
- Web Site: http://library.uncg.edu/
- Advisor
- David Knight
Abstract: The isomers obtained by protonation of the isopropenylcyclopentadienyl anion undergo reactions on standing which change the relative percentages of each isomer in the mixture. The suitability of tetracyanoethylene as a trapping agent is confirmed by the internal consistency of the relative percentages of the Diels-Alder adducts and isomers. Trapping of the isomer mixture with tetracyanoethylene yields three stable Diels-Alder adducts. The adducts were isolated by fractional crystallization and identified by their characteristic nuclear magnetic resonance, infrared spectra, and elemental analyses. The adducts and their relative percentages were: 7-isopropylidene- 5,5,6,6-tetracyanonorbornene (11.4 ± 2.0%), 2-isopropenyl- 5,5,6,6-tetracyanonorbornene (28.9 ± 1.3%), and 3a,6,6- trihydro-4,4,5,5-tetracyanoindene (58.5 ± 3.2%). Protonation of the anion yielded 17 ± 3% dimethylfulvene, 25 ± 2% 2-isopropenyl-l,3-cyclopentadiene, and 57 ± 2% 1-isopropenyl- l,3-cyclopentadiene.
Protonation of the isopropenylcyclopentadienyl anion : trapping of the isomer mixture with tetracyanoethylene
PDF (Portable Document Format)
8455 KB
Created on 1/1/1971
Views: 284
Additional Information
- Publication
- Thesis
- Language: English
- Date: 1971
- Subjects
- Isomerism
- Crystallization
- Rearrangements (Chemistry)