[robert_l]

hello

i have a compound (see attached) and it undergoes a cycloaddition under photochemical conditions to give an intermediate. the intermediate reacts in a thermal condition to give product

i cant work out the intermediate, can u help. i understand that in photochemical conditions there will be a move of etiher 4 or 8 pi-electrons, and in thermal either 6 or 10.

thanks

robert

[movies]

Very interesting question.  I have to ask – are you certain that you have drawn the correct product?  Getting to that product will involve breaking two C–C sigma bonds so it would require more than just electrocyclizations.

[orgopete]

Yes, there must be an error here. The starting material is C12H12O and the product is C12H10O.