97229-08-8Relevant articles and documents
Hypervalent Iodine Iodinative Decarboxylation of Cubyl and Homocubyl Carboxylic Acids
Moriarty, Robert M.,Khosrowshahi, Jaffar S.,Dalecki, Tomasz M.
, p. 675 - 676 (1987)
The hypervalent iodine oxidative decarboxylation of homocubyl and cubyl mono- and di-carboxylic acids is reported; the carboxylic acid is treated with PhI(OAc)2-CCl4-I2 under irradiation conditions and 80-90percent of the derived iodo compound is obtained.
Synthesis of Methylcubane and Cyclopropylcubane. The Cubane-1,4-diyl Route
Eaton, Philip E.,Li, Jianchang,Upadhyaya, Subhash P.
, p. 966 - 968 (1995)
Details for preparation of 1,4-diiodocubane from cubane-1,4-dicarboxylic acid are given.The diiodide is used to generate cubane-1,4-diyl, a nonisolable intermediate.Additions to the diyl are shown to provide for the ready synthesis in good yield of methylcubane, 1,4-dimethylcubane, cyclopropylcubane, etc.
Cubane, Bicyclo[1.1.1]pentane and Bicyclo[2.2.2]octane: Impact and Thermal Sensitiveness of Carboxyl-, Hydroxymethyl- and Iodo-substituents
Dallaston, Madeleine A.,Houston, Sevan D.,Williams, Craig M.
supporting information, p. 11966 - 11970 (2020/08/25)
With the burgeoning interest in cage motifs for bioactive molecule discovery, and the recent disclosure of 1,4-cubane-dicarboxylic acid impact sensitivity, more research into the safety profiles of cage scaffolds is required. Therefore, the impact sensitivity and thermal decomposition behavior of judiciously selected starting materials and synthetic intermediates of cubane, bicyclo[1.1.1]pentane (BCP), and bicyclo[2.2.2]octane (BCO) were evaluated via hammer test and sealed cell differential scanning calorimetry, respectively. Iodo-substituted systems were found to be more impact sensitive, whereas hydroxymethyl substitution led to more rapid thermodecomposition. Cubane was more likely to be impact sensitive with these substituents, followed by BCP, whereas all BCOs were unresponsive. The majority of derivatives were placed substantially above Yoshida thresholds—a computational indicator of sensitivity.
Metal-free efficient, general and facile iododecarboxylation method with biodegradable co-products
Kulbitski, Kseniya,Nisnevich, Gennady,Gandelman, Mark
supporting information; experimental part, p. 1438 - 1442 (2011/07/30)
The development of a novel, efficient and robust method for the general conversion of aliphatic and aromatic carboxylic acids to organic iodides without the use of heavy metals or strong oxidizing agents is reported. Commercially available N-iodoamides were used for both initiation and halogen donation under irradiative conditions. Isolation of the product is extremely simple and the major co-product is removed as a water-soluble biodegradable material. Copyright