Abstract
A convenient procedure to access 1-[(1,1′-biphenyl)-4-yl]naphthalene by the Stevens rearrangement of the aminium salts bearing simultaneously 3-phenylprop-2-enyl and [3-(α-naphthyl)prop-2-ynyl] moieties was developed. During vacuum distillation, the synthesized compounds underwent the domino reaction to afford 1-[(1,1′-biphenyl)-4-yl]naphthalene. On the first step of this reaction, β-elimination of secondary amines gave the conjugated dienyne; on the second step, the electrocyclic reaction of dienyne resulted in cyclic allene intermediate; on the third step, allene intermediate rapidly transformed to 1-[(1,1′-biphenyl)-4-yl]naphthalene via either 1,3- or 1,5-hydrogen shift.
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No human or animal subjects were used in this research.
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Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 6, pp. 1262–1265, June, 2022.
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Chukhajian, E.O., Ayrapetyan, L.V. & Panosyan, G.A. Synthesis of 1-[(1,1′-biphenyl)-4-yl]naphthalene from amines obtained by the Stevens rearrangement of N-[3-(naphthalen-1-yl)prop-2-yn-1-yl]-3-phenylprop-2-en-1-aminium bromides. Russ Chem Bull 71, 1262–1265 (2022). https://doi.org/10.1007/s11172-022-3528-9
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DOI: https://doi.org/10.1007/s11172-022-3528-9