Syntheses and rearrangements of cage molecules related to cubane

Abstract

This article looks at the synthesis of cubane, basketene, miscellaneous homocubane chemistry, snoutene, triqunacene, hypostrophene, tris-homocubane, and catalysis by transition metals.

Carbo-Cages: A Computational Study

“…Particularly, cagelike polyhedral hydrocarbons, (CH) n , are attractive due to their nonclassical carbon bonding, 1 unusual ring strain, 1−9 σaromaticity/antiaromaticity, 3,5,10−12 and their ability to participate in isomerization reactions. 13,14 Illustrative examples of polyhedral hydrocarbons include prismanes and platonic hydrocarbons. The first ones, so-called [m,n]-prismanes, are built of m identical n-membered rings, held together by n single C−C bonds in a regular prism with a D nh symmetry.…”

“…Polyhedranes have awoken interest in the chemical community due to their aesthetically pleasant molecular structures, challenging synthesis, sophisticated structure–energy correlation, and singular physicochemical properties. Particularly, cage-like polyhedral hydrocarbons, (CH) n , are attractive due to their nonclassical carbon bonding, unusual ring strain, − σ-aromaticity/antiaromaticity, ,,− and their ability to participate in isomerization reactions. , …”

Strained bridgehead cage alcohols and derivatives

“…Encouraged by the successful synthesis of cubane and its SCHEME 1 cage compounds, several research groups entered this field. 10 The result of all these activities is a valuable contribution to both synthetic and physical organic chemistry.11…”

Synthesis of trans-4,5-Bis-dibenzylaminocyclopent-2-enone from Furfural Catalyzed by ErCl3·6H2O

“…Functionalized cyclopentenones are important compounds because this structural moiety is found in a large number of natural compounds, including biologically active molecules such as prostaglandins and pesticides, and are also important as very useful synthetic intermediates for the synthesis of bioactive carbocycles . Their importance arises mainly due to the rich chemistry of the enone functionality which allows 1,2- and/or 1,4-additions, cycloadditions, and allylic and α-carbonyl functionalization . Consequentially, a high number of reports concerning functionalized cyclopentenones (approximately 25,000 in SciFinder, with over 8000 chiral examples) are described in the literature.…”