A Stable Naphtho Derivative of Cyclobutadiene

Manifestations of Antiaromaticity in Organic Materials: Case Studies of Cyclobutadiene, Borole, and Pentalene

“…In lieu of steric protection, Cava et al explored increasing the conjugation within the ring fusion (from benzo to napthocyclobutadiene) to impart added stability. [35] After reducing 29 with zinc, the afforded 30 was air, light, and temperature stable. Cava et al rationalized that the additional benzene moiety diminished the cyclobutadienoid character, thereby lending itself to greater stability.…”

“…In lieu of steric protection, Cava et al. explored increasing the conjugation within the ring fusion (from benzo to napthocyclobutadiene) to impart added stability [35] . After reducing 29 with zinc, the afforded 30 was air, light, and temperature stable.…”

“…[34] (b) Synthetic strategy for producing napthocyclobutadiene. [35] [29] (b) Biphenylene, [3]phenylene, [4]phenylene. [51,53] of requisite alkyne precursors in a variety of starting geometries, and the generality of this chemistry which enables expansion into a variety of larger [N]phenylenes such as that shown at the bottom of Figure 2.…”

“… (a) Intramolecular ring closure of 27 affords TMS‐protected benzocyclobutadiene ( 28 ) [34] . (b) Synthetic strategy for producing napthocyclobutadiene [35] …”

Benzazetidines and Related Compounds: Synthesis and Potential

“…Since the early 1960s, interest in the construction of benzo‐fused four‐membered heterocycles has grown for several reasons such as the possibility of benzenoid bond fixation resulting from the small ring fusion, the study of valence isomerism, and the possibility to obtain anions, isoelectronic with naphthalene, with potential aromatic properties. The first reported example for the synthesis of the benzazetidine structure was accomplished starting from 3‐phenyl‐4 H ‐benzo‐1,2,3‐triazine ( 1 ), derived from N ‐( o ‐aminobenzyl)aniline, described in Scheme .…”