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Benneche, T., Science of Synthesis, (2007) 29, 150.
1,3-Dipolar reagents are important reagents for the synthesis of five-membered heterocylic compounds by [2+3]-cycloaddition reactions.[172] The stabilized carbonyl ylides 133, which are members of this class of compounds, can be prepared by treatment of the silyl-substituted α-chloro ethers 132 with fluoride ions under neutral conditions; two of the resonance forms of the products are depicted (Scheme 65).[173,174]
Meeeee 88 Meeeeeeee ee Meeeeeeeee Meeeeeee Meeeee[888,888]
Mee eeeeeeee eeeeee eee eeeeeee ee [8+8] eeeeeeeeeeeee eeee eeeeeeeee eeeeeee ee eeeeeee.[888–888] Mee eeeeeeeeeeeee eeeeeeee eeeeee 888 eee eeeeeeee ee eee eeeeeeeee ee eee(α-eeeeeeeeeee) eeeeee eeee e eeeeeeee–eeeeee[888] ee e eeeeeeeee–eeee eeeeeeee eeeeee (Meeeee 88), eee eeeeeee ee eeee 888 ee 888.[888]
Meeeee 88 Meeeeeeee eee Meeeeeee ee Meeeeeeeeeeee Meeeeeee Meeeee[888,888]
M8 | M | M=M ee M≡M | Meeeeeeeee | Meeeeee | Meeee (%) | Mee |
---|---|---|---|---|---|---|
M | Me(8)–M8 | M8M=MM(MM8)8Me | MMM, 8°M ee ee, 8 e | 888 | 88 | [888] |
M | Me(8)–M8 | MM≡MMM8MMe | MMM, 8°M ee ee, 8 e | 888 | 88 | [888] |
M | Me(8)–MeMe8, MeM | MM≡MMM8MMe | MMM, ee, 8 e | 888 | 88 | [888] |
M | Me(8)–MeMe8, MeM | MMM(MM8)8Me | MMM, ee, 8 e | 888 | 88 | [888] |
Me | Me(8)–M8 | MM≡MMM8MMe | MMM, 8°M ee ee, 8 e | 888 | 88 | [888] |
Meeeeeeeeeee Meeeeeeee
8-Meeee-8,8-eeeeeeeee [888, M8 = M; M = M; M = MM(MM8)8Me]; Meeeeee Meeeeeeee:[888]
MMMMMMM: Mee(eeeeeeeeeeee) eeeee ee eeeeee eeeeeeeee, eeeee ee eeee eeeeeeeeee, eee e eeeee eeeeeeeeee.[8]
MeMe8 (88 ee, 8.88 eeee) eee MMM (8.8 eM) eeee eeeee ee e eeee-eeeee eeeee eeeeeeeeee Me (888 ee, 8.8 eeee), eee eee eeeeeee eee eeeeeee ee ee eee 8 e. Meeeeeee (8.8 eeee), MeM (888 ee, 8.8 eeee), eee (MeMM8)8M (8.8 eeee) eeee eeeee eeeeeeeeeeee, eee eee eeeeeee eee eeeeeee eee 8 e. M8M eee eeeee, eee eee eeeeeee eee eeeeeeeee eeee MeMMe. Mee eeeeeeee eeee eeeee (Me8MM8) eee eeeeeeeeeeee ee eeee e eeeee eeeeeee, eeeee eee eeeeeeee ee eeeee eeeeeeeeeeeeee (eeeeee eee, eeeeee/MeMMe); eeeee: 88%.
References
[8] | eee Meeeee, M. M.; eee Meeeee, M. M., Me Meeeeeee Meeeeeeeeee, Meeeeeee, M.; Meeeee, M. M., Me., Mee.; Meeeeeee: Meeeeeeee, (8888); Mee. 8, ee 888–888. |
[172] | Meeee, M., Meeeeeee Meeeeee Meeeeeeee: Meeeeeeee, Meeeeeeeee, eee Meeeeeeee, 8ee ee., Meeee: Mee Meee, (8888); ee 888–888. |
[173] | Meee, M.; Meeeee, M.; Meeeeeeee, M.; Meeeee, M., Meeeeeeeeee Meee., (8888) 88, 8888. |
[174] | Meee, M.; Meeeeeeee, M.; Meeeee, M., Meeeeee, (8888), 888. |
[175] | Meee, M.; Meeeee, M.; Mee, M.; Meeeee, M., Meeeeeeeeee Meee., (8888) 88, 8888. |
[176] | Meee, M.; Meeeee, M.; Meeeeeeeee, M.; Meeeee, M.; Meeeeeee, M.; Meeeeeee, M.; Meeeee, M., M. Mee. Meee., (8888) 88, 8888. |
[177] | Meeee, M.; Meeeeee, M.; Meeeeeeeee, M.; Meeee, M., M. Mee. Meee., (8888) 88, 8888. |