A convenient and high-yielding three-step synthesis of 8-halonaphthalene-1-carbonitriles has been achieved by ring opening of 1H-naphtho[1,8-de][1,2,3]triazine with the corresponding halides as the key step. Naphthalene-1,8-dicarbonitrile also has been synthesised from 8-bromonaphthalene-1-carbonitrile via palladium-catalysed cyanation of the aryl bromide. The crystal structures of 8-chloronaphthalene-1-carbonitrile, the A polymorph of the bromo analogue, and naphthalene-1,8-dicarbonitrile are isomorphous with orthorhombic symmetry. The B polymorph of the bromo compound and the iodo analogue are also isomorphous, but with monoclinic symmetry. In all of the halo carbonitriles, the molecules are disordered with respect to the location of the halogen atoms and the nitrile groups. There are no intermolecular X···NC interactions in any of the solids.

中文翻译：

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8-halonaphthalene-1-carbonitriles 和naphthalene-1,8-dicarbonitrile 的合成和晶体学

通过1H-萘并[1,8-de][1,2,3]三嗪的开环，以相应的卤化物为关键，实现了8-卤代萘-1-腈的方便、高产的三步合成步。Naphthalene-1,8-dicarbonitrile 也由 8-bromonaphthalene-1-carbonitrile 通过钯催化的芳基溴氰化合成。8-氯萘-1-腈的晶体结构、溴类似物的A多晶型物和萘-1,8-二腈的晶体结构是同晶的，具有正交对称性。溴化合物和碘类似物的 B 多晶型物也是同晶型的，但具有单斜对称性。在所有卤代腈中，分子在卤素原子和腈基团的位置上都是无序的。在任何固体中都不存在分子间 X···NC 相互作用。