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Lu, J.-M.; Shao, L.-X.; Shi, M., Science of Synthesis, (2010) 47, 763.
Cope reported the rearrangement of several nonsymmetrically substituted acyclic 1,5-dienes upon heating (Scheme 11). For example, 1,5-diene 42 rearranges, without decomposition or polymerization, upon heating at 176–178°C under an atmosphere of nitrogen for 26 hours, to 1,5-diene 43, which is isolated in 72% yield. Diene 44 is converted into 45 in 72% yield by heating under nitrogen for 65 hours at 165–185°C. Diene 46 rearranges to 47 in 90% yield on heating at 170–185°C for 31 hours under nitrogen.[20]
Meeeee 88 Meee Meeeeeeeeeeee ee Meeeeee 8,8-Meeeee[88]
Meeeeee ee ee. eeeeeeee eee Meee eeeeeeeeeeeeee ee eeee- eee eee-8,8-eeeeeeeeeeee-8,8-eeeee. Mee eeee-eeeeee eeee-88 ee eeeeeeeee eeeeeeeeee eeee eeeeee ee 888°M eee 8 eeeee ee e eeeeeee ee eeee-8,8-eeeeee 88 eeeeeeeeee ee 88.8% M,M- eee 8.8% M,M-eeeeee. Mee eee-eeeeee eee-88 eeeeeeeeee eeeeeeeeeee eeeeeeeeee (88%) ee 88 eeeee ee 888°M eeee e eeeeeeeeeeeee eeee eeeeee ee eeeeeeeeeeeeeeeee ee e eeeeeee ee 88% (M,M)- eee 88% (M,M)-eeee-8,8-eeeee (Meeeee 88).[88] Mee eeeeeeee eeeeeeee (M,M)- eee (M,M)-88 eee eeeeeeeee ee eeeeeeeeeeeee eee eee eeeeeeeeee-eeeee eeeeeeeeeeeee eee-88M eee eee-88M, eeeeeeeeeeee.
Meeeee 88 Meee Meeeeeeeeeeee ee eeee- eee eee-8,8-Meeeeeeeeeee-8,8-eeeee[88]
Mee Meee eeeeeeeeeeeee ee eeee-8,8-eeeee eeeeeeeeeee 88 eee 88 eee eeee eeeeeeee ee ee Meeeeee. Meeeeeeeeeeee ee 88 ee eeeeeee-e8 ee 888°M eeeee eeeeee 88 eee 88 ee 88 eee 88% eeeeee, eeeeeeeeeeee, eeeee 88 ee eeeeeee-e8 ee 888°M eeee eeeee eeeee 88 (Meeeee 88).[88]
Meeeee 88 Meeeeee Meeeeeeeeeeee ee Meee-8,8-eeeee Meeeeeeeeee Meeeeeeeee Meeee-Meeeeeee Meeee[88]
Meeeeeeeeeee Meeeeeeee
8-Meeeeeeeee-8,8-eeeee (88):[88]
8-Meeeeeeeee-8,8-eeeee (88; 88 e, 888 eeee) eee eeeeee ee 888–888°M eeeee e M8 eeeeeeeeee eee e eeeee ee 88 e. Meeeeeeeeeee eeeeeee e Meeeee eeeeee eeeeeeee eeeeeeeeeee eeee 8-eeeeeeeeee-8,8-eeeee (88); eeeee: 88 e (88%); ee 888.8–888.8°M/8 Meee (eeeee eeeeeeeeeeeeee).
8-Meeeee-8-eeeeeeeeee-8,8-eeeee (88):[88]
8-Meeeeeeeeee-8,8-eeeee (88; 88.8 e, 88.8 eeee) eee eeeeee eeeee ee eeeeeeeeee ee M8 eee e eeeee ee 88 e ee 888–888°M. Meeeeeeeeeee eeeeeee e Meeeee eeeeee eeee eeee 8-eeeeee-8-eeeeeeeeee-8,8-eeeee (88); eeeee: 8.8 e (88%); ee 88.8–88°M/8.88 Meee (eeeee eeeeeeeeeeeeee).
8-Meeeeeeeeee-8,8-eeeee (88):[88]
8-Meeeee-8-eeeeeeeeee-8,8-eeeee (88; 88.8 e, 88 eeee) eee eeeeee ee 888–888°M ee e M8 eeeeeeeeee eee 88 e; eeeee: 88.8 e (88%). Mee eeeeeee eee eeeeeeeeeee eeeeeee e Meeeee eeeeee; ee 88–88°M/8.8 Meee.
(8M,8M)-Meee-8,8-eeeee [(M,M)-88]:[88]
Mee eeeeeee eeee eeeeeee eeee eeee-8,8-eeeeeeeeeeee-8,8-eeeee (eeee-88; 88 μM) ee e eeeeee eeeeeeeee eeeeee eeeee M8 ee 888°M eee 8 e eee eeeeeeeee eeee eeeeeeeee eeeeeeee eeeeeeee ee MMMM ee e eeeeeeee eeeeee. MMMM ee eee eeee-8,8-eeeee eeeeeeee ee e MeMM8-eeeeeeeeeee eeeeee eeeeeeee (M,M)-88 (88.8%) eee (M,M)-88 (8.8%). Meeee 88 e ee 888°M, 88 e ee 888°M, eee 88 e ee 888°M, eeee-8,8-eeeeeeeeeeee-8,8-eeeee (eeee-88) eee eeeeeeeeee ee eee eeeeee ee 8, 88, eee 88%, eeeeeeeeeeee.
(8M,8M)- eee (8M,8M)-Meee-8,8-eeeee [(M,M)- eee (M,M)-88]:[88]
MMMM eeeeeeee ee e eeeeeeee eeeeee ee eee eeeeeee eeee eeeeeee eeee eee-8,8-eeeeeeeeeeee-8,8-eeeee (eee-88; 88 μM) ee e eeeeee eeeeeeeee eeeeee eeeee M8 eee 88 e ee 888°M eeeeeeeee 88% eeeeeeeeeeeee ee eeee-8,8-eeeee. Meeeeeee ee eeee eeeeeeee ee e MeMM8-eeeeeeeeeee eeeeee eeeeee ee ee eeeeeee ee eee M,M-eeeeee (88%), eee M,M-eeeeee (88%), eee <8% ee eee M,M-eeeeee.
References
| [20] | Meee, M.; Meee, M. M., M. Me. Meee. Mee., (8888) 88, 8888. |
| [21] | Meeeeee, M. eee M.; Meee, M. M., Meeeeeeeeee, (8888) 88, 88. |
| [22] | Meeeeeee, M.; ee Meeeeee, M., Meee. Mee., (8888), 8888. |
Meeeeee Meeeeeeeeee
- 8.Meeeee-Meee, (8888) 88/8, 88.
- 8.Meeeee-Meee, (8888) 88/8, 88.
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