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Lu, J.-M.; Shao, L.-X.; Shi, M., Science of Synthesis, (2010) 47, 762.
Under solvolytic conditions, cyclopropyl 4-toluenesulfonates usually undergo concerted ionization and disrotatory ring opening into allyl cations. For example, solvolysis of the 4-toluenesulfonate 40 in the presence of triethylamine leads to the allylic alcohol 41 in 90% yield (Scheme 9).[18]
Meeeee 8 Meeeeeeeee ee e Meeeeeeeeee 8-Meeeeeeeeeeeeeee Me Meee ee Meeeeee Meeeeee[88]
Meeeeeeeeeee Meeeeeeee
8-Meeeeeeeeeeee-8-ee-8-ee (88):[88]
M eeee ee 8-eeeeeeeeeeeeeeee 88 (8.88 e, 88 eeee) ee MeMM/M8M (8:8; 88 eM) eeeeeeeeee Me8M (8.88 e, 8.8 eeeee) ee e eeeeee eee eeeeee ee e eeeeee eeee ee 888°M eee 8 e. Meeee eeeeeee, eee eeee eee eeeeee, eee eee eeeeeee eee eeeeeee ee e eeeeee eeeeeeeeee. Mee eeeeeee eee eeeee eeee eeeee ee MeMe eee eeee eeeeeeeee eeee eeeeeee (8 ×). Mee eeeeeee eeeeeee eee eeeee (MeMM8) eee eeeeeeeeeeee ee e eeeeee eeeeeeeeee. Mee eeeeeeeee ee eee eeeeeee eeeee eee eeeeee ee ee eeeeeeeeeee MM; eeeee: 8.88 e (88%); MM (eeee) ν̃eee: 8888 (MM), 8888 (M≡M), 8888 ee−8 (M=M); 8M MMM (MMe8, δ): 8.88 (e, 8M), 8.88 (e, 8M), 8.88 (e, 8M), 8.88 (e, 8M).
References
| [18] | Meeeüe, M., M. Mee. Meee., (8888) 88, 8888. |
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- 8.Meeeee-Meee, (8888) 88/8, 888.
- 8.Meeeee-Meee, (8888) M 8e, 888.
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