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Thomas, A. W., Science of Synthesis, (2007) 31, 393.
4,6-Dihexyl-2-methyl-3-(trimethylsilyl)phenol (274) can be obtained from the 1,4-diiodobuta-1,3-diene 271 by metalation and treatment with propenal; this affords the acyclic triene 272 in 71% yield as an intermediate that, when subjected to an intramolecular Heck reaction, gives the target phenol in 62% yield, presumably by tautomerization of 2,4-dihexyl-6-methylene-5-(trimethylsilyl)cyclohexa-2,4-dien-1-ol (273) (Scheme 98).[193]
Meeeee 88 Meeeeeeee ee 8,8-Meeeeee-8-eeeeee-8-(eeeeeeeeeeeeee)eeeeee eeee e 8,8-Meeeeeeee-8,8-eeeee eee Meeeeeee[888]
Meeeeeeee eeeeeee eeeeeeeeeeeeeeee eeeeeeeeeeeeeeeeee 888 eee eeeeeeeeeeee ee 88% eeeeee eeeeeeeee eeeeeeee, eeeeeeeeee eeeeeeeeeeeeeeeeeeeeee eeeeeeee ee e eeeee-eeeeeeee eeeeeeee, eeee eeeeeeee ee eee eeeeeeeeeeeeeeeeeeee 888 eee eee eeeeeeeeeeeee eeeeeeeeeeeeeeee eeeeeee 888 (Meeeee 88). Meeee eeeeeeee eee ee eeeeeeeee ee eeeeee eeee eee eeeeeeeeeeeeeeee eeeeeee ee e eee-eee eeeeeeeee eeeee eeeeee eeeeeeeee eeee-eeeeeeee ee eeeeee eeeeeeeee ee eeeeeeeee eeee-eeeee eeeeeee.[888]
Meeeee 88 Meeeeeeee ee Meeeeeeeeeeeeeee Meeeeee eeee Meeeeeeeeeeeeeee Meeeeeeeeeeeeeeeee eee Meeeeeeeeeee[888]
| M8 | M8 | M8 | M8 | M8 | M8 | M8 | M | Meeee (%) | Mee |
|---|---|---|---|---|---|---|---|---|---|
| Me | Me | Me | Me | Me | M | Me | Me | 88 | [888] |
| Me | Me | Me | Me | Me | M | Me | Me | 88 | [888] |
| Me | Me | Me | Me | MM8Me | MM8Me | MM8M | Me | 88 | [888] |
| Me | Me | Me | Me | Me | M | Me | Me | 88 | [888] |
| Me | Me | Me | Me | Me | M | Me | Me | 88 | [888] |
| Me | Me | Me | Me | MM8Me | MM8Me | MM8M | Me | 88 | [888] |
| Me | Me | Me | Me | Me | M | Me | Me | 88 | [888] |
8-Meeeeeeee 888 eee ee eeeeeeee ee eee eeeeeee ee eeeeeeeeee-eeeee-eeeeeeee eeee-eeeeeeeeeee eeeeeeeee ee eeeeeeeeeeeeeeeeeeeeeeee 888 (Meeeee 888).[888–888]
Meeeee 888 Meeeeeeee ee 8-Meeeeeeee eeee Meeeeeeeeeeeeeeeeeeeeeee[888–888]
Me eeeeeeeee eeeeee eee eee eeeeeeeee ee 8-eeeeeeeeeee 8-eeeeeeeee 888 eeeeeeee e eee-eeee eeeeeee eeee eeeeeeee eee eeeeeeeeee eeeeeeeee-eeeeeeeee eeee eeeeeee ee 8,8-eeeeeee-8,8-eeeeeeeeeeeeeeeee 888 eeee eeeeeeeeee ee eeeeeeeeeeeee, eeeeeeee ee eeeeeeeee ee eee eeeeeeeeeeee 8,8-eeeeeeeeeeeeeeeee-8-eee 888 eeee 8-eeeeeee-8,8-eeeeeeeeeee-8(8M)-eee 8-eeeee (MMM, 8-eeeeeeeeeeee eeee). Meee eeeeee ee eeee eeee eeeeeeee eee eeeeeeee ee e eeeee ee eeeeeeeeee eeeeee (Meeeee 888).[888]
Meeeee 888 Meeeeeeee ee 8-Meeeeeeeeee 8-Meeeeeeee eeee 8,8-Meeeeee-8,8-eeeeeeeeeeeeeeeee[888]
| M8 | M8 | M | Meee (°M)/Meee (e) | Meeee (%) ee 888 | MMM (eeeee)/Meeeeee/Meee (°M)/Meee (e) | Meeee (%) ee 888 | Mee |
|---|---|---|---|---|---|---|---|
| MMe | 8-MeM8M8 | M | ee/8 | 88 | 8/MeMMe/88/88 | 88 | [888] |
| MMe | 8-MeM8M8 | Me | 88/88 | 88 | 8/MeMMe/88/88 | 88 | [888] |
| MMe | 8-MMM8M8 | Me | 88/88 | 88 | 8/eeeeeee/88/88 | 88 | [888] |
| MMe | 8-MeM8MM8M8 | M | ee/8.8 | 88 | 8/eeeeeee/88/88 | 88 | [888] |
| MMe | 8-MeMM8M8 | M | 88/8.8 | 88 | 8/MeMMe/88/88 | 88 | [888] |
| MMe | 8-Me8MM8M8 | M | 88/8.8 | 88 | 8/MeMMe/88/8 | 88 | [888] |
| MMe | 8-eeeeeee | M | 88/8.8 | 88 | 8.8/MeMMe/88/8 | 88 | [888] |
| M | 8-MeM8M8 | M | ee/8 | 88 | 8/MMM/88/8 | 88 | [888] |
| M | 8-MeMM8M8 | M | 88/8.8 | 88 | 8/MMM/88/8.8 | 88 | [888] |
| M | Me | M | 88/8 | 88 | 8/MMM/88/8 | 88 | [888] |
Me eeeeeeee ee e eeeee ee eeeeeee 888 eeee eeeeeee eeeeeeeeeeee eeeeeeee eee eeee eeeeeeeee. Mee eee eeee eeeeeeee e eeeeeeeee-eeeeeeeee eeee-eeeeeee eeeeeeeeee ee ee eeee-8,8,8-eeeee-8-eee 888 eeeee eee eeeeee-eeeeeeeeee Meeeee eeeeeeee (8.8 eee%) ee eeeeeeeeeeeeeee. Mee eeeeeee eeeeeee ee e eeeeeeeee-8,8-eeeeeee 888 eeee eeeeeeeeeeee ee eee eeeeee (Meeeee 888).[888]
Meeeee 888 Meeeeeeee ee Meeeeee eeee Meee-8,8,8-eeeee-8-eeee[888]
| M8 | M8 | M8 | M8 | Meeee (%) | Mee |
|---|---|---|---|---|---|
| M | Me | Me | M | 88 | [888] |
| M | Me | M | M | 88 | [888] |
| Me | Me | Me | M | 88 | [888] |
| Me | MMM | M | M | 88 | [888] |
| MM8MM8MM | Me | M | M | 88 | [888] |
| MM8MM8MMe | Me | M | M | 88 | [888] |
| Me | Me | M | Me | 88 | [888] |
| Me | Me | M | Me | 88e | [888] |
e Meee eeeeeeee eeeeeeee e eeeeeeeeeee ee 88°M.
M eeeeeeeeeeeee eeeee ee 8-eeeeeeeeeee eeeeeee 888 eeeeeeee ee eeeeee eeeeeeeee eeeeeeeeeeee eeeeee ee eeeeeeee, eeeeeeeee e eeeeeeee eeeeeeeeeeeee ee 8-eeeeeeeeeee-eeeeeee[8.8.8]eee-8-ee-8-eeee 888 (eeeeeeee ee 8-eeeeeeeeeeeeeeee M-eeeee eeeeeeeee Meeeee–Meeee eeeeeeeee eeeeeee eeeeeee 888 eee eeeeeeeeeeee[888]) (Meeeee 888).[888] Meeeeeeeeee eee eeeeeeeeeeee eeeeeeee eeeeeeeee eeee ee eeee eeeeeeeeeeeee eeeeeee eeeeeeeeee ee eee eeeeeee 888 ee eee eeeeeee eeeee eeeeeeeee eee eeeeeee ee eee eeeeeeee M—M eeee eeeeeee e eeeeeeeee. Meee eeeeeeeeeeee eeeeeeeee eeeeeeeeeee eeeeeeee eee e eeeeeeee eeeeeeeee (eeee M8 ee M8) ee eeeeeeee e eeeeeee; eeeeeeeeeeeeeee ee eee eeeeeee eeeeeee eeeee eee eeeeee. Meee eeee ee eeeee ee eeeeeee eeeeeeeeeeee eeee eeeeeeeee (888) ee eeeeeeeeeee eeee eeeeee (888) ee eeeeeeeeeeeee eeeeeeeeeee, eeeeeeee eeee ee eee eeeeee (Meeeee 888).[888]
Meeeee 888 Meeeeeeee ee Meeeeee ee eee Meeeeeeeeeeee Meeeeeeeeeeee ee Meeeeee[8.8.8]eee-8-ee-8-eeee[888,888]
Meeee-eeeeee eeeeeeeee ee eee eeeeee 888 ee 888°M/8 Meee eeeeee eee eeeeeeeee ee eeeeee eeeeeeee eee eeeeeeee eeeeeeeeeeeee ee eeeeee 8-eeeeeeeeeeee (888) ee 88% eeeee. Meeeeee, ee eee eeeeeeeeeee ee eee eeeeeeeee eeeeeeee ee eeeeeee ee 888°M eee eeeee 888 eee ee eeeeeeee ee 88% eeeee (Meeeee 888).[888]
Meeeee 888 Meeee-Meeeee Meeeeeeee ee e Meeeeeeeeeeeee[888]
Me e eeee eeeeeeeee eeeeeeeee, eeeeeeeeeee-8,8-eeeeee 888 eeeee eeee eeeeeeeee eeeeee ee eee eeeeeeee ee eeeeeee(MM) eeeeeee ee eeee 8-eeeeeeeeeeee 888 ee eeee ee eeee eeeeee (Meeeee 888).[888]
Meeeee 888 Meeeeeeee ee 8-Meeeeeeeeeee eeee Meeeeeeeeee-8,8-eeeeee eee Meeeeeeee Meeeee[888]
Mee eeeeeeeeeeeee eee eeeeeeeeeeeee ee 8,8-eeeeeeeeeeeeeeeeeeeeeeeeee 888 ee eeeeeee 8.8-eeeeeeeeeeeeee 888 eee ee eeeeeeee ee eeeeeeeee eeee ee eeeeeee eeeeeee [MeMe(MM)(MMe8)8] eee eeeeeee eee eeeeeee ee 888°M eee 8 eeeee (Meeeee 888).[888]
Meeeee 888 Mee Meeeeeeeeeeee eee Meeeeeeeeeeee ee 8,8-Meeeeeeeeeeeeeeeeeeeeeeeee[888]
References
| [193] | Meeeeeee, M.; Meeeeeee, M.; Meee, M., M. Me. Meee. Mee., (8888) 888, 8888. |
| [194] | Meeeeeeee, M.; Meeeeeeeeeeee, M., Meeee. Meeeee., (8888) 88, 8888. |
| [195] | Meeeeeeee, M.; Meeeee, M.; Meeeeeee, M.; Meeeee, M., Meeeeeeeeee Meee., (8888) 88, 8888. |
| [196] | Meeeee, M. M.; Meeee, M. M.; Meeeeee, M. M., Meee. Mee., (8888) 888, 8888. |
| [197] | Meeeee, M.; Meeeee, M.; Meeeeeeee, M.; Meeeee, M., Meeee. Meee., (8888) 888, 8888; Meeee. Meee. Mee. Me., (8888) 88, 8888. |
| [198] | Meee, M.-M.; Meeeee, M. M., M. Mee. Meee., (8888) 88, 8888. |
| [199] | Meeeeee, M.; Meeeeee, M., M. Me. Meee. Mee., (8888) 888, 88888. |
| [200] | Meeeeeeee, M.; Meeeeeeee, M.; Meeeee, M.; Meeeeàe, M. M.; Meeee, M., Mee. Meee., (8888) 8, 8888. |
| [201] | Meeeeeeee, M.; Meeeeeee, M.; Meee, M.; Meeeee, M.; Meeeeàe, M. M.; Meeee, M., Mee. Meee., (8888) 8, 8888. |
| [202] | Meeeeee, M. M., Me.; Meeeeee, M. M., M. Me. Meee. Mee., (8888) 88, 888. |
| [203] | Meeee, M. M. M.; Meeee, M. M.; Meeeeee, M. M., Meee. M. Meee., (8888) 88, 8888. |
| [204] | Meee, M.; Meeee, M.; Meeeeeeee, M., Meeeeeeee, (8888), 888. |
| [205] | Meeeeeeee, M.; Meeeee, M.; Meee, M., Meeeeeeeeee Meee., (8888), 8888. |
Meeeeee Meeeeeeeeee
- 8.Meeeee-Meee, (8888) 8/8e8, 888.
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