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Preparation of Stable Bicyclic Aziridinium Ions and Their Ring-Opening for the Synthesis of Azaheterocycles
Published on: August 22, 2018
1,3-Diiodo-azulene-2-carbonitrile
Sebastian Förster1, Wilhelm Seichter, Edwin Weber
1Institut für Organische Chemie, TU Bergakademie Freiberg, Leipziger Strasse 29, D-09596 Freiberg/Sachsen, Germany.
Abstract:
In the title compound, C11H5I2N, the two iodine-atom substitutents with their large atomic sizes lead to short intra-molecular I⋯H distances (3.01 Å). In the crystal, the tris-ubstituted azulene system forms π-stacks [centroid-centroid distance = 3.6343 (11) Å] along the a-axis direction, showing the characteristic azulene inter-action mode between the electron-rich five-membered ring and the electron-deficient seven-membered ring. I⋯I [3.9129 (2) Å] non-covalent contacts are observed along with weak C-H⋯N and C-H⋯π. bonds.
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The IUPAC and common names of amides are derived from the parent carboxylic acid, by replacing the suffix “oic acid” and “ic acid,” respectively, with “amide.” In the following example, the IUPAC name ethanamide is derived from ethanoic acid, and the common name, acetamide, is obtained from acetic acid.
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Azide ions act as good nucleophiles and react with unhindered alkyl halides to form alkyl azides. Alkyl azides do not participate in further nucleophilic substitution reactions, thereby eliminating the chances of polyalkylated products. Alkyl azides are reduced by hydride-based reducing agents, like lithium aluminum...

