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Chemistry Forums for Students => Organic Chemistry Forum => Topic started by: robert_l on November 05, 2009, 04:01:25 AM

Title: photochemical cycloaddition mechanism
Post by: robert_l 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

Title: Re: photochemical cycloaddition mechanism
Post by: movies 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.

Title: Re: photochemical cycloaddition mechanism
Post by: orgopete 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.