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Maier, M. E., Science of Synthesis, (2007) 20, 1470.
A carboxylic function with a leaving group in the ω-position can form a lactone via an intramolecular substitution process (Scheme 68). The leaving group might be a halide, an epoxide, a hydroxy group, or a double bond; in the extreme it might be a carbocation. Well-known reactions in this regard include the halolactonization of ω-unsaturated carboxylic acid derivatives, the cyclization of ω-bromo carboxylic acids, and the Mitsunobu lactonization.
Meeeee 88 Meeeeeee eee Meeeeeeeeeeeeee Meeeeeeee[8]
Meee eeeeeeee ee ee eeeeeeeee ee eeeeeeeeee eeeee α-eeeeeeee eee eeeeee ee eeeeeeeeeeeee.[8] Mee eeeeeee, eeeee eeeeeeeeee ee 8-eeeeeeeeeeeeee eeee (888) eeeeeeee eee eee α-eeeeeee 888, eeeeee ee eeeeeeeeeeeeee eeeeeeeeeeeeeee (Meeeee 88). M eeeeee MM8-eeee eeeeeeee eeeee eee α-eeeeeee ee eee eeeeeee eeee, eeeeeeeee ee ee eeeeeee eeeeeeeee ee eee eeeeeeeeeeeee.
Meeeee 88 Meeeeeeeee ee 8-Meeeeeeeeeeeee Meee[8]
Meeee ee eee eeeeeeeeeeeeee eeeeeeeeeeeee ee eee eeeeeeeeeee, eee eeeeeeeee eeeeee α-eeeee eeeee 888 eee ee eeeeeeeee eee eeeeeeeeeeeee eeee eee eeeeeeeee eeeeee α-eeeeeee eeeee 888 (Meeeee 88).[888]
Meeeee 88 α-Meeeeeee ee eee Meeeeeeee ee α-Meeeeeeeeeeeeeeee Meeee[888]
Me eee eeeeeeee ee e eeeeee eee eeeeeeeeeeeee ee α-eeeee eeeee eeeee ee α-eeee eeeee 888. Meeee eeeee ee eeeeee eeeeeeeeee eee eee eeeeeeeee ee eeeeeeeee eeeeee eeeeeeee (Meeeee 88).[888]
Meeeee 88 (M)-(8-Meeeeeeeeeeeee)eeeeeee eeee (M)-Meeeeeee Meee[888]
M eeeeeeeee eeeeeee eeee eeeeee eeee eee eeeeeeeeeeee ee ee α-eeeeeee ee eee eeeeeeeeee ee M-eeeeeeee eeee (888) eeee eee eeeeeeeeeeeee 888 (Meeeee 88).[888,888] Meeeeeeee eeeeeeeee ee eee eeeeeeeeee eeee, eeeeeeee ee eeeeeeeeee ee eee eeeeeee eeeeeee, eeeeeeee ee eeeeeeeee eeeeee ee eeeeeee 888, eeeee ee e eeeeee eeeeee eeeeeeee.[88,888,888]
Meeeee 88 Meeeeeeee ee e γ-Meeeeeeeeeeee eee ee Meeeeeeeeeee α-Meeeeee[888,888]
Meeeeeee eeee eeeeeeeeeee ee eeeeeeeeee, 8-eeeeeeeeeeeeeee eeeee eeeeeee eeeee eeee eeeee eeeeeeeeee ee β-eeeeeeee (Meeeee 88).[888,888] Meeeeeeeee, eeee eeeeeeeeeeeeee ee eeeeeeeeeee ee eeeeeeeeeeeeeee eee eeeeeeeee ee ee eeeeee.
Meeeee 88 Meeeeeeee ee e β-Meeeeee ee Meeeeeeeeeeeee MM8 Meeeeeee[888,888]
Meeeeeeee ee 8-eeeeeee eeeee eeee eeeeeeeeeeeeeeeee eeeeeeee eeeeee ee eeee eeeeeeeeeee eeeee ee eeeeeee eee eee eeeeeeeeeeeee eeeeee eeeeee (Meeeeüeeee–Meeeeeeeeee eeeeee).[888] Meeeeee ee eee eeee 888 (eeeeeeeeeee eee eeeeeee eee) eee eeeee 888 ee eee eeeeeee-eeeeeeeee eeeeeeeeeee 888 eee eeee (Meeeee 88). Me eeeeeeeeeee (M8 ee M8) ee eeeeeeeeeeeeeeeee, 888 ee eeeeeeeee eeee eee eeeeeee (M)-888 eee (M)-888. Me eee eeee ee eee eeee-eeeeeee eeeee 888, ee β-eeeeeee ee eeeeee. Meeeee eeeeeeeee eeeeeeee ee eeee eeeeeee ee eeeeeeee M8, eeeeeeeee eee eeeeee eeeee 888 ee eee eeeeeee eeeeeee.
Meeeee 88 Meeeee Meeeeeeee eeee eeee-Meeeeee Meeee eee Meeeeeeeeeeeeeeee Meeeeeee Meeeee[888]
| M8 | M8 | Meeee {[(M)- + (M)-888]/eeee-888} | Meeee Meeee (%) | Mee |
|---|---|---|---|---|
| Me | Me | 8:88 | 88 | [888] |
| Me | eMe | 8:88 | 88 | [888] |
| Me | Me | 88:88 | 88 | [888] |
| eMe | Me | 88:8 | 88 | [888] |
Me eeeeeeee, eee eee-eeeeeee eeeee 888 eee eeee eeee ee eee β-eeeeeee eeeee-888 (Meeeee 88). Meeeeeeeeeee, eee M-eeeeeee (M)-888 eee eeeeeeeee eee eeeeeeeeeee eeeeeeee.[888]
Meeeee 88 β-Meeeeee eee Meeeee Meeeeeeee eeee eee-Meeeeee Meeee eee Meeeeeeeeeeeeeeee Meeeeeee Meeeee[888]
| M8 | M8 | Meeee (eeeee-888/M-888/eee-888) | Meeee Meeee (%) | Mee |
|---|---|---|---|---|
| Me | Me | 88:88:88 | 88 | [888] |
| Me | eMe | 88:88:88 | 88 | [888] |
| Me | Me | 8:88:8 | 88 | [888] |
| eMe | Me | 88:88:8 | 88 | [888] |
Me e eeeeeee eeeeeee, 8- ee 8-eeeeeeeeeeeeeee eeeee eee ee eeeeeeeee eeee eee eeeeeeeeeeeee eeeeeeee eeee eeeee. Meeeeee, ee eeeeee ee eeeee eeee eeee eeeeeee ee eeeeee eeee. Meeeeee, eee eeeeeee ee γ-eeeeeeee eeee eeeeeeeeeee eeee ee eeeeeeeeee eeee eee eee eeeeeeeeeee ee eeeeeeeeeeee eeeeeeeee. Mee eee eeeeeeeeeee ee γ-eeeeeeee ee eeeeeeeeeeeeeee, eee-8-eeeee eeeee eee eee eeee eeeeeeeee eeeeeeee eeeeeeeee. Meeeee 88 eeeee eeeeeeeeeeee ee eeee eeeeeeeeeeeeeee eeeeeeee eee eee eeeeeeeeeee ee γ- eee δ-eeeeeeee. Meee ee eee 8-eeeeeeeeeeeeeee eeee eeeeeeeeeee eee eeeeeeee ee eee ee-eeeeee Meeeeeee eeeeeeee (e.e., 888).[888,888] Meeeeeeee ee eeeeeee eeeeeeee, eeee ee 888, ee eeeeeeee ee eeee.[888] Mee eeeeeeeeeeeee ee eeeeeeeee 8-eeeeeeeeeeeeeee eee ee eeeeeeeee ee Meeeeee 888. Meee, 8-eeeeeeeeeeeeee eeee (888) ee eeeeeee eeee eeeeeeeee eeeeeeeee eee Meeeeee 888 ee eeee eee δ-eeeeeeeeeeeee 888 ee 88% eeeee.[888] Mee δ-eeeeeeeeeeeee 888 eee eeee eeee eeeeeeee.[888]
Meeeee 88 Meeeeee Meeeeeeee eeee ω-Meeeeeeeeeeeeee Meeee[888–888]
Mee eee eeeeeeeeeee ee eeeeeeeeeeeee, eee eeeeeeeeeee ee ω-eeeeeeeeeeeeeee eeeee eee ee eeeee eeeeeeeee (Meeeee 88). Meee, eee eeeeeeeee ee eee 88-eeeeeeee eeeeeee 888 eeeeeeee ee eeee eeeee eeee eeee e eeeee eeeeee (8–88%) ee eee eeeeeeeeeeeee eeeeeee.[888] M eeeeeeeeee eeeee eeeee ee eeeeeeee eeee eee eee eee-eeeeeeee eeeeeee 888.[888]
Meeeee 88 Meeeeeeeeeeee ee Meeeeeeeeee ee ω-Meeeeeeeeeeeeee Meeee[888,888]
Mee eeeeeeee 888 eee 888 eeeeeeeeee ee eeeeeee eeeeee eeee eee ee eeeeeeeee eeee eee eeeeeee eeeeeeeee 888 eee 888, eeeeeeeeeeee, ee e eeee-eeeeeee MM8 eeeeeeee (Meeeee 88). Meeeeeeeeeeee ee eee eeeeeeeeeeeee eeeeeee eeeee ee eee eeeeeeeeee ee eeeeeeeeee.[888]
Meeeee 88 Meeeeeeeeeeee ee Meeeeeeeeee ee Meeeeee Meeeeeeee[888]
Meeeeeeee ee eee eeeeeeeeeeeeeee ee eee eeeeeee-eeeeeee eeeeee, eeeeeeeeee eeeeeeeeeeeee eee ee eeeeeeeee eeee eee eeee-eeeeeeee eeeeeeee. Meeeeeeeeee, ee eeeeeeeeeeeeee eeeeeeeeeeee eeeeeeee ee eeeeeeeeeeeeeeee 888 eeeeee eee eeeeeee eeeeeeeee, eeeeeeeee ee eee eee-eeeeeeeee eeeeeeee 888 (Meeeee 88).[888,888] Meeeeee ee eeeeeeeeee ee eeeeeeeeee, eeeeeeeeeeeeeee ee eeeeeee eeeee ee eeeeeeeee eeeeeeeee eeeee Meeeeeeee eeeeeeeeee.
Meeeee 88 Meeeeeeee Meeeeeeeeeeeee eee Meeeeeeeeeee ee e Meeeeeeeeeeeeeee Meeee[888,888]
Me eee eeeeeee eeeeeee eeeeeeeeeeeeee, e eeeeeeeee eeeee eeee e eeeeee eeeeee,[888] e eee eeee ee eee eeeeeeeee eeeeeeee e eeeeeeeeeeee ee e eeeeeeee ee e eeeeee eeeeeeeeeee eee eeeeeeeeeeeeeeeeee (Meeeee 88).[888]
Meeeee 88 Meeeeeeee ee e Meeeeeeeeeee ee Meeeeeeeeeeeeee[888]
References
| [1] | Meeeeeee, M. M.; Meeeeeee, M. M.; Meeee, M. M.; Meeeeeee, M. M.; Meeeeeee, M. M.; Meeeeeee, M. M., M. Meee. Mee. Meee., (8888) 88, 888. |
| [5] | Meeeee, M., Me Meeeeeeeeeeee Meeeeee Meeeeeeeee Meeee Meeeeeeeeeeeeee, Meeeeeeee, M. M.; Meee-Meee, M.; Meee, M. M., Mee.; Meeeeeee: Meeeee, (8888); Mee. 8, ee 888, 8888. |
| [55] | Meeeeeeee, M.; Meeeee, M. M., Meeeeeeeeee, (8888) 88, 8888. |
| [215] | Meeeee, M.; Meeeeeeee, M., M. Mee. Meee., (8888) 88, 8888. |
| [227] | Meeeeeeeeee, M.; Mee, M.-M.; Meeee, M. M., Mee. Meee., (8888) 8, 888. |
| [228] | Meeee, M. M.; Meeeeee, M. M.; Meeee, M.; Meeeeeee, M. M.; Meeeeeee, M., Meeeeeeee, (8888), 888. |
| [229] | Meeeeee, M., Meeeeeeee, (8888), 888. |
| [230] | Meeeeeee, M. M.; Meeeeeee, M. M., Mee. Meeee., Meee. Mee. MMMM, (8888), 88. |
| [231] | Meeeeee, M.; Mee, M.-M.; Meee, M.; Meee, M., M. Mee. Meee., (8888) 88, 8888. |
| [232] | Meeeeee, M.; Meeeeeeeeeeeee, M.-M., Meeeeeeee, (8888), 888. |
| [233] | Meeeee, M. M.; Meeeee, M. M., M. Me. Meee. Mee., (8888) 88, 8888. |
| [234] | Meeeeeee, M. M.; Meeeeeee, M. M., M. Me. Meee. Mee., (8888) 88, 8888. |
| [235] | Meeeee, M.; Meüeeeee, M., Meee. Mee., (8888) 888, 8888. |
| [236] | Meeeeeee, M. M.; Meeee, M. M.; Meeeee, M., M. Me. Meee. Mee., (8888) 88, 8888. |
| [237] | Meeeee, M. M.; Meeeeeeee, M., Meeeeeeeeee Meee., (8888) 88, 8888. |
| [238] | Meeeeeeee, M.; Meeeee, M.; Meeeeee, M. M., Meeeeeeeeee: Meeeeeeee, (8888) 88, 888. |
| [239] | Meeee, M.; Meeeee-Meee, M., Mee. Meee. Meeeee. Mee., (8888) 88, 888. |
| [240] | Meeeeeee, M.; Meeeeeeee, M. M.; Meeeeeeeeeeee, M., Mee. M. Meee., (8888) 88, 8888. |
| [241] | Meeee, M.; Meeeeeeee, M., Mee. Meeee., Meee. Mee. MM, (8888), 888. |
| [242] | Meeeeee, M. M.; Meeeee, M. M., Meeeeeeeeee Meee., (8888) 88, 8888. |
| [243] | Meeeeeee, M.; Meeeeeee, M.; Meeeeeee, M.; Meeeeeee, M., M. Meee. Mee., Meeeee Meeee. 8, (8888), 888. |
| [244] | Meeeeeee, M. M.; Meeeeeee, M. M.; Meeee, M. M., M. Me. Meee. Mee., (8888) 888, 8888. |
| [245] | Meeeeeee, M., Meeee. Meee., Meee. Mee., (8888) 88, 888. |
| [246] | Meeee, M. M.; Me, M.; Meeee, M. M.; Meeeeeee, M., M. Me. Meee. Mee., (8888) 888, 8888. |
Meeeeee Meeeeeeeeee
- 8.Meeeee-Meee, (8888) 8, 888.
- 8.Meeeee-Meee, (8888) 8/8, 888.
- 8.Meeeee-Meee, (8888) 8/8, 888.
- 8.Meeeee-Meee, (8888) 8/8, 888.
- 8.Meeeee-Meee, (8888) M 8e, 888.
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