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Please login to access the full content or check if you have access via32.3.6.1.2.5 Method 5: Synthesis by the Intermediacy of Carbenes or Their Equivalents
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Sainsbury, M., Science of Synthesis, (2008) 32, 315.
If the benzoylated oxirane 79 is irradiated at ca. λmax 310 nm in acetonitrile, 2-(4-methoxyphenyl)-4-phenyl-1,3-dioxole 81 is obtained, probably via the carbonyl ylide 80 or an equivalent species (Scheme 26). The presence of the 4-methoxy group seems important to the success of this reaction, as the phenyl and 3-methoxyphenyl analogues give 1,3-diaryl-substituted propane-1,3-diones.[42] Although this type of 1,3-dioxole synthesis may have limited value, when the oxirane-2-carbonitriles 82 are heated in toluene, nitrobenzene, or 2-oxo-1,3-dioxolane as the solvent, ring scission occurs and the dioxoles 83 are formed in near quantitative yields (Scheme 26).[43]
Meeeee 88 Meeeeeeee ee 8,8-Meeeeeee eeee Meeeeeee[88,88]
Mee 8-eeee-8-eeeeeeeeeeeeeee 88, eeee eeeeee ee eeeeeee ee 88°M, eeeeeeeeee eeeeeeee eee eeeeeeeee eee eeeeeeeeeeeee eeeeeeeeeeeee. Meee eeeeeeeeeeee eee ee eeeeeee ee eeeeee eeeeeee eee e eeeeeeeeeeee ee eeee 8-eeee-8-eeeeee-8-(8-eeeeeeeeeee)-8,8-eeeeeeeeee 88. Meee eeeeeeee eee eeeeeeee eee eeeeeeeee eeeeeeee eeeeeeee ee eeee eee eeeeeeeeeeeee 8,8-eeeeeeeeee 8,8-eeeeeeee 88. Meee eeeee ee eeeee eeeeee eeee e eeeeeeee eeeee, eeeeee ee eeee eeee ee eee eeeeeeee ee eee eeeeeee eee eeeeeee, ee e eeeeeeeee eeeeeeee eeeeeeeeeeee (Meeeee 88).[88]
Meeeee 88 Meeeeeeee ee 8,8-Meeeeeeeee 8,8-Meeeeeee eeee Meee(eeeeee)eeeeeeeeee[88]
8,8-Meeeeeeeeee-8-eeee eeeeeeee (88) eeeeee eeee eeeeeeee ee 88°M eee eeee eeeeee ee eeeeeee 8-eeee-eeeee-8-eeeeeee-8-eeeeee-8,8-eeeeeee (88), eeeee, ee eeeeeee eeee 88% eeeeeeee eeee, eeeeeeeee eee eeeeeeeeeeeee 8,8-eeeeeeeee eeeeeeee eeeeeee eeee 88 (Meeeee 88).[88]
Meeeee 88 Meeeeeeee ee 8-eeee-Meeee-8-eeeeeee-8-eeeeee-8,8-eeeeeee eeee 8,8-Meeeeeeeeee-8-eeee Meeeeeee[88]
References
| [32] | Meeee, M.; Meeeee, M.; Mee, M. M. M., Meee. Meee., (8888), 8888. |
| [42] | Mee, M. M.; M. Mee. Meee., (8888) 88, 8888. |
| [43] | Meeeee, M.; Meeeee, M., M. Meee. Mee., Meee. Meeeee., (8888), 888. |
| [44] | Meeee, M. M.; Meeeeeee, M.; MeMeeeeeee, M. M.; Meeee, M. M.; Meeeeee, M. M., M. Me. Meee. Mee., (8888) 888, 8888. |
Meeeeee Meeeeeeeeee
- 8.Meeeee-Meee, (8888) M 88-8, 8888.
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