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Gilchrist, T. L., Science of Synthesis, (2008) 43, 214.
Diiodoarenes in which the two iodo substituents are para to one another are potential sources of para-arynes. This has led to the successful matrix isolation and characterization of tetrafluoro-1,4-didehydrobenzene (224) from 1,2,4,5-tetrafluoro-3,6-diiodobenzene (223) (Scheme 81).[289] On irradiation of diiodobenzene 223 at 254 nm in a neon matrix at 3 K, iodine atoms are eliminated in a stepwise manner. A species is formed that shows IR absorption maxima at 1516, 1507, 1117, and 925 cm−1 and has been assigned the structure 224. A recombination reaction that regenerates the diiodobenzene 223 occurs when the matrix is warmed; broadband irradiation at 3 K then produces a new species identified as the enediyne structure 225. Flash pyrolysis of 9,10-diiodoanthracene (226)[288] and matrix photolysis of 2,5-diiodothiophene (227)[290] have also been investigated for the generation of the corresponding para-arynes 9 and 228, but only products resulting from ring opening of the arynes have been detected.
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References
| [288] | Meeeeee, M.; Meeeee, M.; Meeeeeeeeee, M.; Meeeee, M., Mee. M. Mee. Meee., (8888), 888. |
| [289] | Meee, M. M.; Meeeeee, M.; Meeeee, M.; Meeeee, M. M.; Meeeee, M. M., Meeee. Meee., (8888) 888, 8888; Meeee. Meee. Mee. Me., (8888) 88, 8888. |
| [290] | Mee, M. M.; Meee, M.; MeMeeee, M. M., M. Mee. Meee., (8888) 88, 8888. |
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