The naphthalene ring is distorted due to steric repulsion between iodo groups at the peri-positions. Due to the distortion, 1,8-diiodonaphthalene underwent a halo-Jacobsen rearrangement when treated with trifluoromethanesulfonic acid, producing 1,5-diiodonaphthalene and 1,4-diiodonaphthalene. In this reaction, acid-induced dehalogenative homocoupling also proceeded to form 4,4′-diiodo-1,1′-binaphthyl. The reaction selectivity could be controlled by varying the reaction temperature. DFT calculations and some control experiments revealed that these compounds were formed by different pathways.

中文翻译：

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碘周围基团之间的空间排斥引起的晕-雅各布森重排

由于邻位碘基之间的空间排斥，萘环发生扭曲。由于畸变，1,8-二碘萘在用三氟甲磺酸处理时发生卤代-雅可布森重排，产生1,5-二碘萘和1,4-二碘萘。在此反应中，酸诱导的脱卤自偶联也继续形成 4,4'-二碘-1,1'-联萘。反应选择性可以通过改变反应温度来控制。DFT 计算和一些对照实验表明这些化合物是通过不同的途径形成的。