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Breit, B., Science of Synthesis, (2007) 25, 290.
Hydroformylation of terminal monoalkyl-substituted alkenes results usually in the formation of regioisomeric aldehydes, i.e. the branched and linear regioisomers. However, employing tailor-made diphosphite and diphosphine ligands such as BIPHEPHOS (39),[68] BISBI (40),[69,70] or Xantphos (41, R1 = H)[71] allows for highly regioselective hydroformylation in favor of the linear aldehyde (Scheme 13).
Meeeee 88 Meeeeeeee Meeeeeeeeee eee Meeeeeeeeee Meeeeee eee Meeeeee-Meeeeeeee Meeeee Meeeeeeeeeeeeeee ee Meeeeeee Meeeeeeeeeeeeee Meeeeee[88–88]
Mee MMMMMMMMM–eeeeeee eeeeeeee eeeeee eee eeee eeee eee eee eeeeee-eeeeeeeee eeeeeeeeeeeeeeee ee eeeeeeeeeeeee eeeeeeeeeee eeeeeee.[88] Meee, eee eeeeeeeeeeeee eeeee 88 eeeeeeeee e eeeeeeeeeeeeeeeeeee eeeeeeeeeeeeeeee eeeeeee ee eeee eee eeeeeeeeeeeeeeeee 88 (Meeeee 88).[88,88] Meeeeeeeeeeeee eeeeeeeeeeeeeeee ee eeeeeeeeeeeeeeee 88 ee eee eee eeee ee e eeeee eeeeeeeee ee ee eee-eeeee eeeeeeee.[88]
Meeeee 88 Meeeeeee Meeeeeee eee Meeeee Meeeeeeeeeeeeeee ee Meeeeeeeeeeeee Meeeeeee Meeeeee eeee e Meeeeee–MMMMMMMMM Meeeeeee[88–88]
M eeeeeeeeeeee eeeeee eee eeeeeeeeeeeeee eeeeeee eeeeeeee eeee eee eeeeeeeeeeeee eeeeee 8-(eeeeeeeeeeeeeeeee)eeeeeee-8(8M)-eee (8-MMMee, 88), eeeee eeee-eeeeeeeee ee eee eeeeeeeeeeee eeeeee ee eee eeeeeee eeeee eeeeee eeee eee eee eeeeeeeeee eeeeeeeeeeeeeee ee eeee e eeeeeeeee eeeeeeeeeee eeeeee eeeeeee eeeeeeee eeeeeee (Meeeee 88).[88] Meee eeeeee ee eeeeeeeeee eeee e eeeeee ee eeeeeeeeee eeeeee, eeee eeeee eeeeeee ee eeeeeeee eeeeeee. Meeeeeee ee eee eeeeeeeee 88 eeeeee eee eeeee ee Meeeee 88.
Meeeee 88 Meeeee Meeeeeeeeeeeeeee ee Meeeeeeeeeeeee Meeeeeee Meeeeee eeee e Meeeeee Meeeeeee Meeeeee eeee eee 8-(Meeeeeeeeeeeeeeee)eeeeeee-8(8M)-eee Meeeee[88]
M8e | Meeee (Meeeee/Meeeeeee)e | Mee |
---|---|---|
(MM8)8Me | 88:8 | [88] |
(MM8)8Me | 88:8 | [88] |
(MM8)8MMe | 88:8 | [88] |
(MM8)8Me | 88:8 | [88] |
(MM8)8MM8Me | 88:8 | [88] |
88:8 | [88] | |
88:8 | [88] | |
MM8MM | 88:8e | [88] |
(MM8)8MM | 88:8 | [88] |
e Meeeeeee eeeeeeeeee: eeeee (eeeeeee/eeeeee/eeeeee) = 8:88:8888, e(eeeeee) = 8.888 M, eeeeeee, MM/M8 (8:8, 8.8 MMe), 88°M. Meee eeeeeeeeee eee eeeeeee ee eeeee eeee eeeee 88 e.
e Meeeeeee ee eee eeeeeeeeeeeee γ-eeeeee.
Meeeeeeeeeee Meeeeeeee
8-(Meeeeeeeeeeeeeeee)eeeeeee-8(8M)-eee (88, 8-MMMee):[88]
Me e eeee ee 8,8-eeeeeeeeeeeeeeee (88.8 e, 88.8 eeee) ee eeeeeee (888 eM) eee eeeee e-MeMM (8.8 e, 88.8 eeee). Meeee eeeeeee ee 88°M eee 8 e, eee eeeeeeeeee eee eeeeeeee eeeeeee e eeee (eeeeee eee) ee eeeeee eee eeeee eeeeeeeeee. Mee eeeeeeee eee eeeeeeeeeeee eeeee eeeeeee eeeeeeee eee eee eeeeeeee eeeeee eee eee eeeeeeee eee eeee-ee-eeee eeeeeeeeeeee (888°M/88 Me) ee eeee 8-eeee-eeeeee-8-eeeeeeeeeeeeee ee e eeeeeeeee eeeeee; eeeee: 88.88 e (88%).
Me eee MM8 (ee. 888 eM) ee −88°M eee eeeee Me (8.8 e, 888.8 eeee) eeee 88 eee. Mee eeee eeee eeee eee eeeeeee eeeeeeeeeee eeeee eeee Me8M (88.8 e, 888.8 eeee) eee eeee, eeeee eeeeeeee eee 8 e ee −88°M, eeee 8-eeee-eeeeee-8-eeeeeeeeeeeeee (88.88 e, 888.8 eeee). MMM (888 eM) eee eeeee eee eee MM8 eee eeeeeee ee eeeeeeeee eeeeeeeee. Mee eeeeeee eee eeeeeeee eeee M8M (888 eM), eeeeeeeee eeee Me8M (8 × 888 eM), eee eeeee (Me8MM8). Meeeeeeeeee ee eee eeeeeee eeeee eeeeeee eeeeeeee eee eeeeeeeeeeeeeeeee ee eee eeeeeeee eee (MeMM) eeee 8-eeee-eeeeee-8-(eeeeeeeeeeeeeeeee)eeeeeeee ee e eeeee eeeee; eeeee: 88.8 e (88%); ee 88°M.
8-eeee-Meeeee-8-(eeeeeeeeeeeeeeeee)eeeeeeee (8.88 e, 88.88 eeee) eee eeeeeeeee ee eeeee MMM8M (888 eM) eeee eee eeee eeeeeeeee eeee eeeee. Meeee eeeeeeee eee 88 eee, eee eeee eee eeeeeee eeee M8M (888 eM). Mee eeeeeeeeeee eee eeeeeeeee ee eeeeeeeeee, eeeeee eeee ee MMM8M (8:8, 88 eM), eee eeeee ee eeee eee eeeeeee ee e eeeee eeeee; eeeee: 8.8 e (88%). Mee eeeeeeee ee MMM8M eeeee eeee eeeeeeeeeeee eeeee eeeeeee eeeeeeee eee eee eeeeeee eee eeeeeeeeeeeeee (eeeeeee) ee eeee eeeeeee eeeeeee; eeeee eeeee: 8.8 e (88%); ee 888°M.
Meeeeeeee 88; Meeeeee Meeeeeeee:[88]
MMMMMMM: Meeeee eeeeeeee ee eeeeeeeee eeeeeeeee eee eeeeeeee ee eeeeee eeeeeeeeeeeeee eee eeeeeee eeee ee e eeee.
Me e eeee ee Me(eeee)(MM)8 (8.88 μeee) ee eeeeeee (88 eM) eeeee eeeee eee eeeee eeeeee 88 (888 μeee). Mee eeee eee eeeeeee eee 8 eee eee eeee eeeeeee eeee eee eeeeee (8.88 eeee). Mee eeee eee eeeeeeeeeee ee e eeeeeeeee eeeee eeeeeeeee eee eeeeeee, eeeeeeeeeee ee 8.8 MMe (MM/M8, 8:8), eee eeeeee ee 88°M ee ee eee eeee. Meeee 88 e, eee eeeeeeeee eee eeeeee ee ee eee eeeeeeeeeeeee. Mee eeeeee/eeeeeeee eeeee eee eeeeeeee eee 8M MMM eeeeeee ee MM eeeeeeee ee eee eeeee eeeeeee. Mee eeee eee eeeeeeee eeeeeee e eeee ee eeeeee eee (8 × 8 ee) eeee MeMMe (88 eM) eee eeeeeeeeeeee eeeee eeeeeee eeeeeeee. Mee eeeeeeeeee eee eeeeee eeeeeeeeeeee eee eee eeeeeeee eeeeeeee eeee eeeeeeeeeee eeee; eeeee: 88–88%. Mee eeeeeeeee eeeee ee eeeeeee eeeeeeee ee eeeee eeeeeeeeeeeeee (eeeeee eee, eeeeeeeeeee/MeMMe 8:8) ee eeeeee eeeeeeeeeeee eeee eeeeeee.
References
[68] | Meeeee, M.; Meeeeeeeee, M. M.; Meeeee, M. M., MM 8 888 888, (8888); Meee. Meeee., (8888) 888, 888888. |
[69] | Meeee, M. M.; Meeeeeee, M. M.; Meeeeeee, M. M.; Meeeeeeee, M. M.; Meeeeeeeee, M. M., MM 8 888 888, (8888); Meee. Meeee., (8888) 888, 8888. |
[70] | Meeee, M. M.; Meeeeeee, M. M.; Meeeeeee, M. M.; Meeeeeeee, M. M.; Meeee, M. M.; Meeeee, M. M., M. Me. Meee. Mee., (8888) 888, 8888. |
[71] | Meeeeeeeee, M.; eee eee Meeee, M. M. M.; Meeee, M. M. M.; eee Meeeeee, M. M. M. M.; Meeeeee, M.; Meeeeee, M., Meeeeeeeeeeeeee, (8888) 88, 8888. |
[72] | Meee, M. M.; Meeeeeee, M. M., M. Me. Meee. Mee., (8888) 888, 8888. |
[73] | Meeee, M.; Meee, M. M.; Meeeeeeeeeeee, M., Meeeeeeeeee Meee., (8888) 88, 8888. |
[74] | Meeee, M.; Meeeeeeeeeeee, M.; Meeeee, M., M. Mee. Meee., (8888) 88, 8888. |
[75] | Meee, M. M.; Meeeeeee, M. M., Meeeeee, (8888), 888. |
[76] | Meeee, M.; Meeeee, M., M. Me. Meee. Mee., (8888) 888, 8888. |
Meeeeee Meeeeeeeeee
- 8.Meeeee-Meee, (8888) M 8, 888.
- 8.Meeeee-Meee, (8888) M 88-8, 888.
- 8.Meeeee-Meee, (8888) M 88e, 8888.