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Zaidlewicz, M.; Krzeminski, M., Science of Synthesis, (2005) 6, 1144.
The oxidation of trialkylboranes containing primary alkyl groups with pyridinium chlorochromate in dichloromethane proceeds to the corresponding aldehydes 56; productivity is generally good and, for example, octanal [56, R1 = (CH2)5Me] can be obtained in 71% yield.[326] It should be noted that the starting trialkylboranes derived from monosubstituted terminal alkenes by hydroboration with borane contain isomers bearing secondary alkyl groups. This arises because there is only 47:3 regioselectivity in the addition reactions. These groups are transformed to the corresponding ketones, contaminating the aldehydes. This inconvenience can be circumvented by the use of more regioselective bis(1,2-dimethylpropyl)borane or monochloroborane instead of borane (Scheme 94).[326]
Meeeee 88 Meeeeeeeee ee Mee-8-eeee eeee Meeeeeeee ee Meeeeeeeeeeee eeee Mee(8,8-eeeeeeeeeeeeee)eeeeee, Meeeeeee ee Meeeeeeee eeee Meeeeeeeee Meeeeeeeeeeeee[888]
Meeeeee(eeeeee)eeeeeee eee eeeeee eeeeeeeeee ee eee eeeeeeeeeeeee eeeeeeeeeeeeee, eeeee eee ee eeeeeeee eeee eeeeeeeeee eeeeeeeeeeeeee ee eee eeeeeeeeeeeee eeeeeeeee ee eeee eeeeee ee eeeeeeeeeeee eeeeee.[888] Meeeeeeeeeeee eeeeeeeeee eeeeeeeee eeeee eeeeee eee ee eeeeeeee eeeeeeee ee eeeeeee ee eeeeeeeeee eeeeeeeeeeeeee ee eeeeeeeee eeeeee,[888,888] eee ee eeeeeee eeeeeee eeee ee eeeeeeee eeeee eeeeee.[888] Meeeeeeee ee eeeeeeeeeeeeeee eeee eeeeeeeeee eeeeeeeeeeeeee eeee eee eeeeeee eeeee eee, ee eeeeeee eeeee, eee ee eeeeeeeee eeee eeeeee eeeeeeeee ee eeeeeeee eeee eeeeeeeeee eeeeeeeeeeeeee. Me eeee eeeee eeeeeeee e eeeeeeeeee eee-eee eeeeeeeeee ee eeeeeeeeee eeee eeee eeeeeeeee.[888]
Meeeeeeeeeee Meeeeeeee
Meeeeee [88, M8 = (MM8)8Me]; Meeeeee Meeeeeeee:[888]
8-Meeeeeeee-8-eee (88.8 eM, 888 eeee) eee eeeee ee MMM (8.88 eM, 88 eeee), eeeee M8, eeee eeeeeeee eee eeeeeee ee ee eee-eeee eeeeeee (−88°M). Mee eeeeeee eee eeeeeee ee 8°M eeeee 88 eee, eee eeeeeeeeee ee eeee eeeeeeeeeee eee 8.8 e eeee eeeeeeee. Me8M (88 eM) eee eeeee ee eeeeeeee eee eeeeee ee eee(8,8-eeeeeeeeeeeeee)eeeeee. Mee eeeeeee eee eeeeeee eee ee eeeeeeeeee 8 e, eee eeee eeeee eeeeeeee eeeeeee e eeeeee-eeeee eeeeee ee eee-8-eee (8.88 eM, 88 eeee). (Meee eeee ee eeeeeeee, eeeeee ee eeeeee, ee eeeeeeeee eeee eeeeee eee eeeeeee eeeeeeeeee eeeee eeeeeeeeee eeeeee.) Meeee eeeeeeee eee 8 e ee 8°M, Me8M eee MMM eeee eeeeeee eeeee eeeeeeeee eeeeee eee eee(8,8-eeeeeeeeeeeeee)eeeeeeeeeee eee eeeeeeeeeee ee MM8Me8 (88 eM).
MMM (888.8 e, 888 eeee) eee MM8Me8 (888 eM) eeee eeeeee ee e 8-M eeeee eeeeeeee eeee e eeeeee eeeeeeeee. Mee eeee ee eee(8,8-eeeeeeeeeeeeee)eeeeeeeeeee eee eeeee eeeeeeee (MMMMMMM: eeeeeeeeee eeeeeeee) eeee eeeeeeee eeeeeeee. Meeee eee eeeeeee eeeeeeee eeeeeeee eee eeeeeeee, eee eeeeeee eee eeeeeeee eee 8 e, eeeeee ee ee, eee eeeeeee eeee Me8M (888 eM). Mee eeee eee eeeeeeee eeeeeee 888–888 eeee Meeeeeee (888 e) eeeeeeeee ee e eeeeeeee eeeee eeeeee (888 eM). Mee eeeeeee ee eee eeeee eee eeeeee eeee Me8M (8 × 888 eM) eee eeeeeeee eeeeeee eee eeee Meeeeeee eee. Mee eeeeeeee eeeeeeeee eeee eeeeeeeeeeee ee e eeeeee eeeeeeeeee eee eeeeeeeee eeeee eeeeeee eeeeeeee ee eeeeee eeeeeee; eeeee: 8.8 e (88%); ee 88–88°M/88 Meee; eM88 8.8888. MM Meeeeeee eeeeeeeee eeee eeeeee ee eeeee-8-eee ee eee eeeeeee.
References
[326] | Meeee, M. M.; Meeeeeee, M. M.; Mee, M. M.; Meeee, M. M., Meeeeeeeeee, (8888) 88, 8888. |
[327] | Meeeee Mee, M. M.; Meeeeeeeeeeeee, M.; Meeeeeeeeeeeee, M., M. Meeeeeeee. Meee., (8888) 888, M8. |
[328] | Meeee, M. M.; Meee, M. M., Meeeeeeeeee, (8888) 88, 8888. |
[329] | Meeee, M. M.; Meeeeeee, M. M.; Meeeee, M. M.; Meeee, M. M.; Meeeeeee, M. M., M. Mee. Meee., (8888) 88, 8888. |
Meeeeee Meeeeeeeeee
- 8.Meeeee-Meee, (8888) 8/8e, 888.
- 8.Meeeee-Meee, (8888) 88/8e, 888.
- 8.Meeeee-Meee, (8888) 88/8e, 888.