Cubane: 50 Years Later

Abstract

Scheme 3. Eaton and Cole's Synthesis of Cubane (1)

Nonconjugated Hydrocarbons as Rigid‐Linear Motifs: Isosteres for Material Sciences and Bioorganic and Medicinal Chemistry

“…Over the years, linear linking has been a classic field of para ‐substituted benzenes and alkynes, due to the plethora of well‐established cross‐coupling reactions . Recently however, certain other hydrocarbons, such as cubane or bicyclo[1.1.1]pentane (BCP) have begun to draw attention due to their remarkable properties . Besides these highly strained, rather unusual hydrocarbons more common moieties are in use, such as bicyclo[2.2.2]octane (BCO) and triptycene (Figure ).…”

Poly(polyhedral)s: synthesis and study of a new class of polyurethanes composed of homocubanes

“…and include cubane as well as benzvalene . The former was successfully incorporated into the backbones of polyacrylates and polyamides, although the solubilities of the respective polymers were relatively limited . Regardless, the cubane units have proved to be functional as they can isomerize to their respective cyclooctatetraenes using Rh catalysts .…”

Structural elucidation of dioxa‐cage compounds from tetrahydroisobenzofuran‐1(3H)‐one: analysis of NMR data and GIAO chemical shifts calculations

“…Over the years, the chemistry and synthesis regarding the polycyclic cage compounds, comprising not only carbocyclic compounds but also heterocyclic analogues, have attracted considerable attention . Their rigid, strained and often symmetric structure provides singular physicochemical properties and bioactivities .…”

“…Over the years, the chemistry and synthesis regarding the polycyclic cage compounds, comprising not only carbocyclic compounds but also heterocyclic analogues, have attracted considerable attention. [1][2][3][4] Their rigid, strained and often symmetric structure provides singular physicochemical properties [5] and bioactivities. [6,7] Besides of being potential substrates for studies of molecular rearrangements [8][9][10] and other reaction mechanisms, [11][12][13] the cage compounds are useful intermediates for the synthesis of more complex molecules, including natural products.…”