An unexpected disorder has been discovered during an X-ray reinvestigation of the crystal structure of the monocyclic hydrocarbon ClsH~s. The study at 80K
Abstract. The 1 ,Cpentamethylene Dewar pyridone l a was synthesized from 2g-undecadiyne (3), aluminium trichloride and phenyl isocyanate. The exclusive formation of l a at the expense of other possible isomers is discussed and tentatively explained by the regiospecific reactivity of the intermediate 4a. Attempts to convert l a into the [5] (2,5)pyridinophan-6-one 2 by irradiation, thermolysis or acid catalysis did not give the desired result. However, on thermolysis and acid catalysis, l a rearranges to the ortho-annelated pyridone 13 in high yield, the structure of which was established by X-ray-crystal structure determination. The mechanism of these reactions is discussed.
ChemInform Abstract Treatment of the AlCl3 complex (III) with the isocyanate (IV) yields the Dewar pyridone (V); the exclusive formation of this regioisomer is ascribed to kinetic factors (MNDO calculations on AlCl3 complexes). The tricyclic compound cannot be converted to the target pyridinophane (VI): on thermolysis or acid catalysis the rearranged product (VII) is obtained, whose structure is ascertained by X-ray analysis (space group Pccn with Z=2).
scite is a Brooklyn-based organization that helps researchers better discover and understand research articles through Smart Citations–citations that display the context of the citation and describe whether the article provides supporting or contrasting evidence. scite is used by students and researchers from around the world and is funded in part by the National Science Foundation and the National Institute on Drug Abuse of the National Institutes of Health.