Serendipitous discovery of new pentacycloundecane molecules

Pentacycloundecanylidene and pentacycloundecanone – hyperconjugatively stabilized carbene and ketone

“…Pentacycloundecane and its various derivatives were experimentally isolated. 51,52 The removal of two hydrogen atoms of one of the -CH 2 groups of the cyclohexyl ring results in the corresponding carbene. The carbene, U1 and U2 are in the singlet state whereas the U3 is in the triplet state.…”

Photochemically Driven Tandem Process in the Construction of a Biscyclopropylcage from 2,5-Dimethoxy-p-benzoquinone and Terminal Acetylenes

“…2 In this regard, cyclobutenes represent an interesting organic framework susceptible to further transformations, enabling the generation of complex polycyclic compounds. 3−5 Cage-like rigid molecules 6,7 are of particular interest due to their unique properties and potential applications in the field of biology or medicinal chemistry. 8,9 In the search for new methodologies to form C−C bonds that would be difficult to access by conventional methods, we explored the photoaddition of alkynes to p-benzoquinones to obtain functionalized fused cyclobutenes en route to more complex molecular scaffolds.…”

“…In fact, light-mediated reactions have proven to be key steps in the synthesis of numerous natural products . In this regard, cyclobutenes represent an interesting organic framework susceptible to further transformations, enabling the generation of complex polycyclic compounds. − Cage-like rigid molecules , are of particular interest due to their unique properties and potential applications in the field of biology or medicinal chemistry. , …”