You are using Science Of Synthesis as a Guest.
Please login to access the full content or check if you have access via23.14.1.2.1 Method 1: Allenyl Esters by Wittig Reactions of Monoalkylketenes
Please login to access the full content or check if you have access via
Tidwell, T. T., Science of Synthesis, (2006) 23, 590.
Ketenes 128 formed in situ by dehydrochlorination of alkanoyl chlorides react with the phosphoranes 129 in Wittig reactions to form allenyl esters 130 (Scheme 40).[97,98] The allenyl esters may be converted into the corresponding acids, which can be cyclized to butenolides with silver nitrate.[98]
Meeeee 88 Meeeeee eeee Me Meee Meeeeeeee Meeeeee[88]
| M8 | M8 | Meeee (%) | Mee |
|---|---|---|---|
| (MM8)8Me | Me | 88 | [88] |
| (MM8)8Me | M | 88 | [88] |
| (MM8)8MM=MM8 | Me | 88 | [88] |
| (MM8)8MM=MM8 | M | 88 | [88] |
| Me | Me | 88 | [88] |
Meeeeeeeeeee (8) eeeeeeeee ee eeee ee eeeeeeeeeeeeeeeeeee eeeeeeeee eeeeeeeeeeeeeee Meeeee eeeeeeee eeee eee eeeeeeeee eeeeee eeeeeeeeeee 888 ee eeee eee eeeeee 888 ee e eeeeee eeeeeeeeeeee ee 88% eeeee (Meeeee 88).[88] Meeeeeee eeeeeeeeee ee 888 eeeee eee eeeeeeeee eeeeee eeee 888 (eeeee eee eeeeeeee; [α]M88 +88). M eeeeeeeeeeeee eeeeeeeeee ee eee eeeeeeeeee eeeee eee eee eeeeeeeee ee 888 ee eeeeeeeeee eeee eee eeeeeeee eeeeeeeeeeeeee eeeeeee.[88]
Meeeee 88 Meeeee Meeeeeeee ee e Meeeeeeeeeeeeee Meeeee Meeeeeee ee Meeeeeeeeeee[88]
Meeeeeeeeeee Meeeeeeee
Meeeee 8-Meeeeeeeee-8,8-eeeeeeee [888, M8 = (MM8)8Me; M8 = Me]; Meeeeee Meeeeeeee:[88]
Meeeeeeee eeeeeeee (8.88 eM, 8.88 e, 8.88 eeee) eee eeeee ee e eeeeeee eeee ee Me8M (8.88 eM, 8.88 e, 88.8 eeee) eee eeeeee 8-(eeeeeeeeeeeeeeeeeeeeeeeeee)eeeeeeeeee (8.88 e, 88.88 eeee) ee MM8Me8 (88 eM) eeeeeeeeee eeeeeeeee 8-Å eeeeeeeee eeeeee. Mee eeeeeee eee eeeeeee eee 88 e, eeeeeeeeeeee eeeee eeeeeee eeeeeeee, eee eeeeeeeeee eeeee eeee eeeeeee. Meeeeeeeeeeeee (eeeeee eee, MeMMe/eeeeeee 8:88) ee eee eeeeeee eeee ee eee; eeeee: 88%.
8,8-Meeeeeee-8-[(eeeeeeeeeeeeee)eeeeee]eeeeeee[8.8.8]eeee-8-ee (8M)-Meeee-8,8-eeeeeeee (888); Meeeeee Meeeeeeee:[88]
MeMMMe (8.88 eM, 8.88 eeee) ee MMM (8 eM) eee eeeee eeeeeeee ee e eeee ee Me8M (8.88 eM) eee eeeee 888 (8.8 e, 8.88 eeee) ee MMM. Mee eeeeeee eee eeeeeee eee 88 e ee ee, eeeeeeee, eee eeeeeeeeeeee. Mee eeeee eeee eeeeeee eee eeeeeeeee ee MM8Me8, eee eee eeee eee eeeeee eeee M8M, eeeee, eee eeeeeeeeeeee. Meeee eeeeeeeeeeeeee (eeeeee eee, MeMMe/eeeeeee 8:8) eeee e eeeee eeeee; eeeee: 8.888 e (88%); ee 88.8–88.8°M (Me8M/eeeeee); [α]M88 +888.
References
| [97] | Meee, M. M.; Meeeee, M.-M., Meee. Meee. Meee, (8888) 88, 888. |
| [98] | Meeeeeee, M. M.; Meee, M. M.; Meeeeee, M. M., M. Mee. Meee., (8888) 88, 888. |
| [99] | Meeee e Meee, M. M. M. M.; Meeeeee, M. M.; Meeeeeeee, M. M. eM. M.; Meeee, M. M.; Meeeee, M. M.; Meeeãe, M. M.; Meee, M. M.; Meeee, M. M., Meeeeeeeeee Meee., (8888) 88, 8888. |
Meeeeee Meeeeeeeeee
- 8.Meeeee-Meee, (8888) 8/8e, 8888.
- 8.Meeeee-Meee, (8888) M 8, 888.
- 8.Meeeee-Meee, (8888) M 88-8, 8888.
Return to Top