On the example of brominating the AlCl3 complex of 2-acetylfuran it was shown that the 4 position in this complex is more active than the 5 position.
The deactivating effect of the acyl group, bound in the AlCl3 complex, is transmitted better through the furan ring than through the thiophene ring. As a result the reactivity of the AlCl3 complexes of carbonyl compounds of the furan series during bromination is lower than that of the corresponding complexes of the thiophene analogs, whereas the reverse ratio of the activities is true for the free carbonyl compounds.
The direction of the bromination of the protonated 2-thiophenecarboxaldehyde and 2-acetothienone (complexes with HSbCl6) differs but slightly from that of the corresponding complexes with AlCl3
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Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 12, pp. 2733–2739, December, 1973.
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Belen'kii, L.I., Gol'dfarb, Y.L. & Gromova, G.P. Reactions of aromatic and heteroaromatic compounds, bearing electron-acceptor substituents. Russ Chem Bull 22, 2666–2671 (1973). https://doi.org/10.1007/BF00926134
- Carbonyl Compound