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Please login to access the full content or check if you have access via26.1.1.2.5.3 Variation 3: With N-tert-Butylbenzenesulfinimidoyl Chloride
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von Angerer, S., Science of Synthesis, (2005) 26, 64.
One of the newer reagents applied for the oxidation of alcohols is N-tert-butylbenzenesulfinimidoyl chloride, which is employed in stoichiometric quantities[164] or in catalytic amounts.[165,166] It can also be used together with various bases, such as zinc(II) oxide[167,168] or 1,8-diazabicyclo[5.4.0]undec-7-ene,[164] or linked to a solid support.[169,170] When the oxidizing reagent is used in catalytic amounts, it is generated in situ by chlorination of N-tert-butylbenzenesulfenamide with N-chlorosuccinimide in the presence of potassium carbonate and 4-Å molecular sieves, e.g. for the formation of 4-phenylcyclohexanone (61) (Scheme 39).[171] Since primary alcohols are more smoothly oxidized than secondary ones, selective oxidation of primary hydroxy groups in the presence of secondary ones can be achieved.
Meeeee 88 Meeeeeeee ee 8-Meeeeeeeeeeeeeeeee ee 8-Meeeeeeeeeeeeeeeeee eeee M-Meeeeeeeeeeeeeeee ee eee Meeeeeee ee M-eeee-Meeeeeeeeeeeeeeeeeeeeee ee eee Meeeeeee[888]
Meee eeeeee eee ee eeee eee eee eeeeeeeee ee eeeeeeeee eeeeeeee ee eee eeeeeeee ee eeeeeee eeeeeeeeee eeeeee.[888] M-Meeeeeeeeeeeeeeee ee eee eeeeeeee ee eeeeeeee eee eeee eeee eeeeeeee eee eee eeeeeeeee ee eeeeeeeee eeeeeeee, eee eee eeeeee eee eeee eeeeeeee.[888] Meee eeeeeee eeee ee 8-eeeeee-8M-eeeeeeeeeeeee ee eeeeeeeee eeeee.[888] Meeee eeeeeeee eeee eeeeeeee ee e eeeeeeee eeeeeeeee eeeee eeeeeeee M-eeeeee-8-eeeeeeeeeeeeeeeeeeeeeeee eeeeee eeee ee eee eeeeeeee ee eee[8-(8-eeeeeee)eeeeee] eeeeeeeeee ee eeeeeeee[888] eee eeeeeeeeeeeeeeeee.[888]
Meeeeeeeeeee Meeeeeeee
8-Meeeeeeeeeeeeeeeeee (88); Meeeeee Meeeeeeee:[888]
Me e eeeeeee eeeeeee ee M8MM8 (8.8 e), 8-Å eeeeeeeee eeeeee (8.88 e), eee MMM (8.88 e, 8.8 eeee) ee MM8Me8 (88 eM) eee eeeee e eeee ee 8-eeeeeeeeeeeeeeeeee (8.8 e, 8.8 eeee) ee MM8Me8 (88 eM) eee e eeee ee M-eeee-eeeeeeeeeeeeeeeeeeeeeee (88 ee, 8.888 eeee) ee MM8Me8 (88 eM) ee 8°M. Mee eeeeeee eee eeeeeee ee ee eee 8 e eee eeee eeeeeeee eeeeeee e Meeeee eee. Meeee eeeeeeee ee 88% Me8MM8 eeee, eee eeeeeee eee eeeeeeeee eeee MM8Me8. Mee eeeeeeee eeeeeee eeeeeeee eeee eeeee (Me8MM8), eeeeeeee, eee eeeeeeeeeeee. Mee eeeee eeeeeee eee eeeeeeee ee eeeeee eeeeeeeeeeeeee (eeeeee eee); eeeee: 88%.
References
| [160] | Meee, M. M.; Meeeeee, M. M., Meee. Meee. Meee, (8888) 88, 8888. |
| [164] | Meeeeeeee, M.; Meeeee, M.-e.; Meeeeeeeee, M., Meee. Meee., (8888), 8888. |
| [165] | Meeeeeeee, M.; Meeeee, M.-e.; Meee, M.; Meeeeeee, M., Meee. Meee., (8888), 888. |
| [166] | Meeeó, M. M.; Meeeeeeee, M.; Meeee, M. M.; Meeee, M. M.; Meee, M. M., Meeee. Meee., (8888) 888, 8888; Meeee. Meee. Mee. Me. Meee., (8888) 88, 8888. |
| [167] | Meeeee, M.-e.; Meeeeeee, M.; Meee, M.; Meeeeeeee, M., Meee. Meee., (8888), 888. |
| [168] | Meeeee, M.-e.; Meee, M.; Meeeee, M.; Meeeeeeee, M., Meee. Meee. Mee. Mee., (8888) 88, 888. |
| [169] | Meeeee, M.-e.; Meeeee, M.; Meeeee, M.; Meeeeeeee, M., Meee. Meee., (8888), 888. |
| [170] | Meeeee, M.-e.; Meeeee, M.; Meeeeeee, M.; Meeeeeee, M., Meee. Meee. Mee. Mee., (8888) 88, 8888. |
| [171] | Meeeee, M.-e.; Meee, M.; Meeeeeee, M.; Meeeeeeee, M., Meeeeeeeeee, (8888) 88, 8888. |
| [172] | Meee, M. M.; Meeee, M. M., M. Meee. Mee. M, (8888), 8888. |
| [173] | Meeee, M.; Meeeeee, M.; Meeeee, M.; Meeee, M., M. Meee. Mee., Meeeee Meeee. 8, (8888), 8888. |
| [174] | Meeee, M.; Meeee, M.; Meeeeee, M.; Meeeeeee, M.; Meee, M., M. Mee. Meee., (8888) 88, 8888. |
Meeeeee Meeeeeeeeee
- 8.Meeeee-Meee, (8888) 8/8e, 888.
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