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Question An \'indolyne\' is another dienophile related to benzyne, which has bee

ID: 1040323 • Letter: Q

Question

Question An 'indolyne' is another dienophile related to benzyne, which has been studied by scientists at UCLA. The indolyne' readily undergoes the Diels-Alder reaction with dienes, including the one shown below. Step 1: The Diels-Alder reaction occurs to give a [2.2.21-bicyclic intermediate. Step 2: However, this is short-lived and is immediately converted to the final fully aromatic compound depicted What name would you give to this latter reaction, which occurs with loss of CO2? (Hint: try drawing the hypothetical reverse reaction of Step 2) Diene 2 Name? -co2 Diels-Alder Me Me Me Indolyne" (dienophile) [2.2.2]-Bicyclic Intermediate

Explanation / Answer

The option D is the correct answer.

It is Retro Diels-Alder Reaction.Since CO2 is a diene it can add to the dienophile (here it is the product)

It will give the [2,2,2]-Bicyclic intermediate.