5773-47-7

Upstream product

• 4233-33-4 4-Phenyl-1,2,4-triazolidine-3,5-dione 
• 629-20-9 1,3,5,7-cyclooctatetraene 

Downstream Products

• 16104-44-2 C₁₆H₁₇N₃O₂ 
• 25863-08-5 7,8-Diazatricyclo<4.2.2.0^2,5>dec-7-en 
• 81599-81-7 N-phenyl-4-oxa-8,9-diazatetracyclo<5.2.2.0^2,6.0^3,5>undec-10-ene-8,9-dicarboximide 

Relevant academic research and scientific papers

The C8H12-Energy Hypersurface Thermolysis of syn- and anti-Tricyclo2,5>octane. Experimental and Theoretical Studies

The thermal behaviour of syn- and anti-tricyclo2,5>octanes 9 and 10 in the gas phase as well as in solution is investigated.Two main products are formed in parallel reactions: cis,cis-1,5-cyclooctadiene (11) and cis,trans-1,5-cyclooctadiene (15), the latter being partly isomerized to 11 under the reaction conditions.Minor products are cis-1,2-divinylcyclobutane (6), trans-1,2-divinylcyclobutane (16) and 4-vinyl-1-cyclohexene (17).Thermolysis of cis-1,2-divinylcyclobutane leads to small amounts of cis,trans-cyclooctadiene, presumably via a four-centre transition state.The tricyclics most likely prefer a stepwise isomerization.The decisive product-controlling factor seems to be the conformational mobility of intermediate diradicals.By comparison with the boat-Cope reaction of divinylcyclobutane the pericyclic six-centre transition state of this rearrangements is shown to lie energetically about 19 kcal/mol below the transition states in the thermolysis of 9 and 10.The azo compound 12 on heating fragments predominantly in a concerted manner in contrast to the photolysis.Theoretical methods are applied to unveil structure and bonding in the supposed intermediate diradicals.