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Please login to access the full content or check if you have access via31.22.1.5.2 Method 2: Photochemical Rearrangement of Nitroarenes
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Rück-Braun, K.; Priewisch, B., Science of Synthesis, (2007) 31, 1349.
2-Nitrobenzaldehyde isomerizes to 2-nitrosobenzoic acid (84) when it is irradiated with ultraviolet light. Similarly, nitroarenes containing a benzylic hydrogen atom ortho to the nitro group undergo intramolecular rearrangement to the corresponding nitrosoarenes. A prominent example is the formation of 2-nitrosobenzaldehyde (86), with accompanying cleavage of the C—O bond, upon irradiation of 2-nitrobenzyl alcohol derivatives 85 (Scheme 42).[127–129]
Meeeee 88 Meeee-Meeeeee Meeeeeeeeeeee ee 8-Meeeeeeeeeeeeeeee eee 8-Meeeeeeeeee Meeeeee Meeeeeeeeee[888–888]
Meeee ee eeee eeee ee eeeeeeeeeeeee, 8-eeeeeeeeeee eeeeeeeeeee eee eeeee eee eeee eeeeeee eeeeeeeeeee eeeeeeeeee eeeeee, eee eee eeee eeeeeeee eee eee eeeeeeeeeeeee eeeeeee ee “eeeee” eeeeeeeee ee eeeeeeeeee eeeeeee.[888,888] Mee eeeeeeeee ee eee eeeee-eeeeeee eeeeeeeeeeeee eee eeee eeeeeee.[888,888] Meeeeeeeeeeee eeeeeeeeeeeeee eee eeee eeee eee eee eeeeeeeeeee ee eeeeeee eeeeeeeee, ee ee eeee eeeeeeee eeeeee eee eeeeeeeee ee eeeeeeeeee. Meee, eeeeeeeeeee ee e eeeeeeeeee eeeeeeee ee (8M)-8-eeeeeee-8-(8-eeeeeeeeeee)eeeee-8,8-eeee-8-ee (88) eeee eeeee ee eeeeeeeeee λ 888 ee eeeee ee eee eeeeeeeee ee ee eeeeeeeeeeee (8-eeeeeeeeeeeee)eeeeeeeeeeee 88 eee ee eeeeeeeeeeeeee eeeeeeeeeeeee; eeee eeeeeeee eeeeeeeee e eeeeee-Meeee–Meeee eeeeeeee eee eeeee 8e-eeeeeee-8,8e-eeeeeee-8M-[8,8]eeeeeee[8,8-e]eeeee-8-eee (88) ee e eeeee ee 88% (Meeeee 88).[888]
Meeeee 88 Meeeeeeeeeeee Meeeeeeeee ee e Meeeeeeeeeee eee e Meeeeeeeee [8+8] Meeeeeeeeeeee[888]
Me eeeee, 8-eeeeeeeeeeeeeeeee ee eeeeeeeeee eeeeeeeeeeeeeee ee 8-eeeeeeeeeeeeee eeee (88) ee 88% eeeee (Meeeee 88).[888]
Meeeee 88 Meeeeeeeeeeee Meeeeeeeeeeee ee 8-Meeeeeeeeeeeeeeee[888]
References
| [127] | Meeeeeeeee, M.; Meeeeeee, M. M.; Meeeeeee, M.; Meeeee, M.; Meeee, M.; Meeee, M., Meeee. Meee., (8888) 888, 8888; Meeee. Meee. Mee. Me., (8888) 88, 8888. |
| [128] | Meeeee, M. M., M. Meee. Mee., Meeeee Meeee. 8, (8888), 888. |
| [129] | Meeeee, M. M.; Meeeee, M. M., MM; Meeeee, M. M.; Mee, M.-M., Me MMM Meeeeeee ee Meeeeee Meeeeeeeeeeeee eee Meeeeeeeeeee, 8ee ee., Meeeeeee, M. M.; Meeee, M., Mee.; MMM: Meee Meeee, MM, (8888), e 88-8. |
| [130] | Me'eeeee, M. M.; Meeeöeee, M. M.; Meee, M., M. Me. Meee. Mee., (8888) 888, 8888. |
| [131] | MeMeeee, M. M.; Meeeee, M. M.; Meeeeeeeeee, M. M., M. Me. Meee. Mee., (8888) 888, 8888. |
| [132] | Meeeeee, M. M.; Meeeeee, M. M.; Meeeeeeee, M. M., Meeeeeeeeee Meee., (8888), 8888. |
Meeeeee Meeeeeeeeee
- 8.Meeeee-Meee, (8888) 88/8, 8888.
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