Question

Please provide the mechanism for the reaction shown below. Include all arrows indicating electron movement/transfer as well as all formal charges, and please explain the mechanism/reaction.

CN CO2Et II NC CO,Et

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Answer #1

Reaction proceeds via free radical .

In first step the benzoyl peroxide produces phenyl free radical with elimination of CO2 .

In next step phenyl free radical abstract H alpha to -CN and Co2Et group because the resulting free radical is stabilized by conjugation.

Further radical undergoes to consecutive cyclization forming 2 fused six membered ring.

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