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,Russian Chemical Bulletin

当前位置： X-MOL 学术 › Russ. Chem. Bull. › 论文详情

Our official English website, www.x-mol.net, welcomes your feedback! (Note: you will need to create a separate account there.)

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
Russian Chemical Bulletin ( IF 1.7 ) Pub Date : 2022-06-28 , DOI: 10.1007/s11172-022-3528-9
E. O. Chukhajian , L. V. Ayrapetyan , G. A. Panosyan

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.

更新日期：2022-06-28

点击分享查看原文

点击收藏

阅读更多本刊新发论文本刊介绍/投稿指南