Abstract
1. 3-(1-Adamantyl)-3-chloropropenal is a useful synthon for obtaining adamantyl-substituted nitrogen heterocycles: 2-(1-adamantyl)quinoline, 2-(1-adamantyl)-6-bromoquinoline, 6-(1-adamantyl)pyrimidine, 1-phenyl-5-(1-adamantyl)pyrazole, and 6-(1-adamantyl)thieno[2,3-e]pyrimidin-4-one. 2. X-ray crystallographic analysis points to the trans configuration of the aldehydic and adamantyl substituents on the C=C double bond in the molecule of 3-(1-adamantyl)-3-chloropropenal which is characterized by near Cs symmetry. A small increase in the C-Cl bond length in this molecule is probably due to a weak intermolecular attractive interaction at a distance of 3.447(2) A.
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