29412-63-3Relevant articles and documents
Cubane Electrochemistry: Direct Conversion of Cubane Carboxylic Acids to Alkoxy Cubanes Using the Hofer–Moest Reaction under Flow Conditions
Collin, Diego E.,Folgueiras-Amador, Ana A.,Pletcher, Derek,Light, Mark E.,Linclau, Bruno,Brown, Richard C. D.
supporting information, p. 374 - 378 (2019/11/19)
The highly strained cubane system is of great interest as a scaffold and rigid linker in both pharmaceutical and materials chemistry. The first electrochemical functionalisation of cubane by oxidative decarboxylative ether formation (Hofer–Moest reaction) was demonstrated. The mild conditions are compatible with the presence of other oxidisable functional groups, and the use of flow electrochemical conditions allows straightforward upscaling.
The cubane cage - A sensible probe for substituent effects on a four-membered ring
Irngartinger, Hermann,Strack, Stefan,Gredel, Frank
, p. 311 - 315 (2007/10/03)
The crystals of methyl 4-fluoro-1-cubanecarboxylate (1), methyl 4-chloro-1-cubanecarboxylate (2) and methyl cubanecarboxylate (5) are isomorphous to each other as are the crystals of methyl 4-bromo-1-cubanecarboxylate (3) and methyl 4-iodo-1-cubanecarboxylate (4). As a result of the space groups P21/m and Pnma, respectively, all molecules lie in a crystallographic mirror plane. Therefore, the methoxycarbonyl group is exactly planar, and the carbonyl fragment is in an eclipsed position to the cubane skeletal bond C2-C7. The electronic effects of the halogen atoms, in particular fluorine and chlorine, give rise to a shortening of the vicinal skeletal bonds. In contrast, the methoxycarbonyl groups causes a lengthening of the vicinal skeletal bonds C2-C6 and C2-C6A which are not in an eclipsed conformation. Ab initio calculations at the 6-31G* level of compounds 1, 2, and 5 confirm the experimental results. VCH Verlagsgesellschaft mbH, 1996.
