Pentacyclo[5.1.0.02,4.03,5.06,8]octane (octabisvalene)

Aromaticity in P8 allotropes and (CH)8 analogues: significance of their 40 valence electrons?

“…The other P 8 structure corresponding to a known saturated (CH) 8 hydrocarbon is the D 2h structure P8-5 , lying 16.5 kcal mol −1 above P8-1 and corresponding to the hydrocarbon octabisvalene. 46 Structure P8-5 has ten essentially equivalent P–P edges of length 2.200 Å. The remaining two edges are those connecting the two bicyclobutane subunits and are slightly longer at 2.232 Å.…”

Organic Synthesis − Art or Science?

“…In second place according to both twc and N T is bond b , which is likewise eliminated by rule 2B, while bond c violates rule 1B. In the actual synthesis, bond b was formed last, which corresponds to disconnecting it first in retrosynthesis …”

Molecules in Silico: A Graph Description of Chemical Reactions

“…Experimentally, many of these types of products were observed to result from reactions of cis -benzene trioxide with methyl phenyl sulfone or other acidified methanes. − …”

“…Given the tris-benzenesulfonates of 8 − 15 above and the corresponding reaction scheme MOLGEN generates carbocyclic tris-σ-homobenzene 16 , disubstituted octabisvalene 17 , disubstituted cubane 18 , and disubstituted cuneane 19 as possible reaction products, as well as some other interesting polycyclics. In fact, compound 17 was synthesized by this sequence of reactions, , while analogs of 16 were obtained by a corresponding sequence . Compounds of types 18 and 19 , however, are not observed in vitro nor expected by a chemist.…”

“…Experimentally, many of these types of products were observed to result from reactions of cis-benzene trioxide with methyl phenyl sulfone or other acidified methanes. [36][37][38] (b) Chemically, for a further ring closure, a good leaving group is required; therefore, we esterify the alcohols formed In fact, compound 17 was synthesized by this sequence of reactions, 36,37 while analogs of 16 were obtained by a corresponding sequence. 38 Compounds of types 18 and 19, however, are not observed in vitro nor expected by a chemist.…”