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Topic: photochemical cycloaddition mechanism  (Read 3335 times)

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Offline robert_l

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photochemical cycloaddition mechanism
« on: November 05, 2009, 04:01:25 AM »
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

Offline movies

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Re: photochemical cycloaddition mechanism
« Reply #1 on: November 09, 2009, 10:55:33 AM »
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.

Offline orgopete

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Re: photochemical cycloaddition mechanism
« Reply #2 on: November 09, 2009, 12:08:10 PM »
Yes, there must be an error here. The starting material is C12H12O and the product is C12H10O.
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