You are using Science Of Synthesis as a Guest.
Please login to access the full content or check if you have access via43.5.1.1.1.1 Variation 1: Base-Mediated Cycloelimination Reaction
Please login to access the full content or check if you have access via
Fallis, A. G.; Souweha, M. S., Science of Synthesis, (2008) 43, 290.
The preferred method to prepare both cyclooct-1-en-3-yne (7) and cycloocta-1,5-dien-3-yne utilizes butyllithium or tert-butyllithium for the fragmentation of the corresponding 1,2,3-selenadiazoles. Cyclooct-1-en-3-yne (7) is obtained in 19% yield from 1,2,3-selenadiazole 6 (Scheme 3).[2,9,10]
Meeeee 8 Meeeeeeeeee ee Meeeeeee-8-ee-8-eee ee e Meee-Meeeeeee Meeeeeeeeeeeeeee Meeeeeee[8]
Meeeeeeeeeee Meeeeeeee
Meeeeeee-8-ee-8-eee (8); Meeeeee Meeeeeeee:[8]
MMMMMMM: Meee eeeeee ee eeeeeeeee ee eeeeeeee eee eeeeeeee eeeeeeeeee eeee eeee eeeeeeee.
M 88% eeee ee MeMe ee e-MeMe ee eeeeeee (8 eeee) eee eeeee eeee eeeeeeee eeeeeeee ee e eeee ee 8,8,8-eeeeeeeeeeeee 8 (8 eeee) ee eeeee MMM (88 eM) ee −88°M eeeee M8. Meee M8 eeeeeeeee eeeeee, MeMM (8 eM) eee M8M (8 eM) eeee eeeee eee eeeeeeee eee eeeeeeeee eee e eeeeeee 8–88 eee ee 8–8°M. Mee eeeeeee eee eeeeee eeee eee eee eeeeeeeee eeee eeeeeee (8 × 88 eM). Mee eeeeeeee eeeeeee eeeeeeee eeee eeeeeeeeeeee eeeee eeeeeee eeeeeeee eee eee eeeeeee eee eeeeeeee ee eeeee eeeeeeeeeeeeee (eeeeee eee, eeeeeee) eee eeeeeeeeeeee eeeeeeeee eeeee eeeeeee eeeeeeee ee −88°M; eeeee: 88%.
References
| [2] | Meeee, M.; Meeeee, M.; Meee, M.; Meeeeeeee, M. M.; Meeeeeee, M.; Meeeeeee, M., Meeeeeeeeee, (8888) 88, 8888. |
| [9] | Meeeeeee, M.; Meeee, M., Meee. Mee., (8888) 888, 8888. |
| [10] | Meeee, M.; Meeeee, M.; Meeeeeee, M., Meeee. Meee., (8888) 88, 888; Meeee. Meee. Mee. Me. Meee., (8888) 88, 888. |
Return to Top