83831-87-2

Upstream product

• 21603-24-7 methyl 3,3-dimethyl-1-phenylcyclopropene-2-carboxylate 
• 83831-84-9 1,2-Dicarbomethoxy-4,4-dimethyl-2-(2-methyl-1-phenyl-1-propenyl)-3-phenylbicyclo<1.1.0>butane 
• 83831-86-1 Dimethyl 2,7-dimethyl-3,6-diphenylocta-2,4(Z),6-triene-4,5-dicarboxylate 
• 83831-84-9 1,4-dicarbomethoxy-2,2-dimethyl-3-phenyl-4-(1'-phenyl-2'-methylprop-1'-enyl)bicyclo<1.1.0>butane 
• 4891-38-7 phenylpropynoic acid methyl ester 

Relevant academic research and scientific papers

Cycloaddition Reactions of Strained Ring Systems. Photochemistry of 1-Phenyl-2-carbomethoxy-3,3-dimethylcyclopropene

The sensitized irradiation of 1-phenyl-2-carbomethoxy-3,3-dimethylcyclopropene produced two novel photodimers.The minor product can be explained in terms of an initial bond formation to give a diradical intermediate.Collapse of the diradical furnishes a tricyclohexane which undergoes a subsequent cycloreversion to give a 1,4-cyclohexadiene derivative.The major photodimer is derived by cyclopropyl ring opening of the initially produced diradical followed by cyclization to give a bicyclobutane derivative.Direct irradiation of 1-phenyl-2-carbomethoxy-3,3-dimethylcyclopropene afforded a mixture of 1-carbomethoxy-3,3-dimethyl-1-phenylallene, 1-carbomethoxy-3-methyl-2-phenylbutadiene, and 2-carbomethoxy-3-methyl-1-phenylbutadiene.The formation of the three products can be rationalized in terms of a vinylcarbene intermediate which inserts into the adjacent methyl group.The product distribution favors cleavage of the carbomethoxy substituted ?-bond of the cyclopropene ring.This regioselectivity can be attributed to a funneling of the excited singlet state of the cyclopropene to the energy surface of the higher lying carbene state.The photochemical and thermal behavior of several hydroxyalkyl substituted cyclopropenes derived from 1-phenyl-2-carbomethoxy-3,3-dimethylcyclopropene was also studied and the results obtained were compared to the reactions in the carbomethoxy series.