72610-67-4

Upstream product

• 20643-23-6 3,5-Dimethylbicyclo<4.2.0>octa-1,3,5-trien-7-on-tosylhydrazon 

Downstream Products

• 72610-72-1 C₁₈H₁₇Br 
• 20643-22-5 4,6-Dimethylbenzocyclobutenone azine 
• 70087-70-6 (Z)-1,1'-Bis(4,6-dimethylbenzocyclobutenylidene) 
• 70080-31-8 (E)-1,1'-Bis(4,6-dimethylbenzocyclobutenylidene) 
• 72610-76-5 C₁₉H₂₀ 
• 72610-84-5 Spiro<4,6-dimethylbenzocyclobutene-1,1'-2',2'-diphenylcyclopropane> 
• 70080-34-1 Spiro<4,6-dimethylbenzocyclobutene-1,1'-2'-phenylcyclopropane> 

Relevant academic research and scientific papers

Benzocyclobutenylidene-Cycloadditions, Reactivity, and Multiplicity

EHT and CNDO/2 calculations on benzocyclobutenylidene (6) are described.Flash pyrolysis of the tosylhydrazone salt 7 affords benzocyclobutene and o-xylene in low yield, along with the formal syn and anti carbene dimers 13 and 14.Condensed-phase reactions were achieved by photolysis of the salt 15.Benzocyclobutenylidene (6) gave rise to the formal carbene dimers 17 and 18.Insertion of carbene 6 into the carbon-hydrogen bonds of 2,3-dimethylbutane produced the benzocyclobutenes 20 and 21 (insertion ratio tertiary:primary = 9:1).Cycloaddition of 6 to olefins gave only spirohexene derivatives 22.Multiplicity studies of 6 with cis or trans olefins indicated that 6 undergoes cycloaddition in a stereospecific manner.Competition experiments using dienes and monoolefins implicate an equilibrium between singlet and triplet 6.Further competition experiments with styrene/para-substituted styrene pairs demonstrated that 6 reacts faster with electron-poor styrenes.Possible explanations for this apparent anomaly are discussed.