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What is the the second reaction known as during the formation of an 'indolyne' which is a dienophile related to benzyne?



. Step 1: It is believed that a [2.2.-bicyclic intermediate forms initially.
Step 2: However, this is short-lived and is immediately converted to the final fully aromatic compound depicted. 



A. Diels–Alder Reaction
B. Anionic Oxy-Cope Rearrangement
C. Indolyne Decarboxylative Extraordinary Attack (IDEA)
D. Retro Diels-Alder Reaction

This question is part of Diels–Alder and Pericyclic Reactions - Prof. Garg
Asked by Catherine halcombe, Last updated: Jul 01, 2020

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2 Answers

V. Barnes

V. Barnes

Answered May 10, 2018

The Retro-Diels-Alder Reaction.

The Retro-Diels–Alder reaction (RDA) is the second microscopic reversed reaction of the Diels–Alder reaction—the formation of a diene and dienophile from a cyclohexene. It can spontaneously be accomplished with heat, or acid or base mediation.

With the right and the appropriate driving force, the Diels–Alder reaction proceeds in reverse, providing diene and dienophile from starting cyclohexene derivatives. This process was known and applied to the detection of cyclohexadienes as early as the year 1929. After reacting with acetylenes through a Diels–Alder/retro-Diels–Alder sequence, it released ethylene and aromatic compounds.

 

John Smith

John Smith

Answered Dec 29, 2016

Retro Diels-Alder Reaction
 

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