Reaction of carboryne with styrene and its derivatives

Styrene as 4π-Component in Zn(II)-Catalyzed Intermolecular Diels–Alder/Ene Tandem Reaction

“…In 2015, Brummond et al reported the mechanistic study of the thermal IMDDA reaction of styrene-ynes, and they found that the naphthalene product was formed via the loss of hydrogen gas from the initially formed cycloadduct A (Scheme a) . As a more straightforward and convenient way to prepare the naphthalene derivatives, the intermolecular Diels–Alder reaction of styrene (4π-component) with an alkyne (2π-component) was much more challenging and highly underdeveloped . Biju et al has taken advantage of benzyne as an effective dienophile to react with styrene under mild conditions (Scheme b) .…”

Generation and reactivity of o-carborynes

“…[29][30][31] In addition to the expected [2 + 2] cycloaddition reaction and/or ene reaction, the extraannular [4 + 2] cycloaddition reaction also takes place in the reactions with o-carboryne, dependent upon the substituents on the exocyclic double bond. 32 The resulting [4 + 2]…”

Formal Insertion of o-Carborynes into Ferrocenyl C–H Bonds: A Simple Access to o-Carboranylferrocenes

“…The resulting [2 + 2] cycloaddition intermediates simultaneously rearrange to cyclooctatetraenocarboranes via thermal [3,3] sigmatropic rearrangement . Further studies show that 3a can undergo [4 + 2] cycloaddition reaction, benzyl C–H bond insertion, and ene reaction with toluene and exocyclic [4 + 2] cycloaddition reaction with styrenes, in which the reactions exhibit a remarkable substituent effect (Scheme ). As an ongoing project, we extended our research to include ferrocene, an intriguing aromatic organometallic complex .…”