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Chapter 27: Q 58. (page 1104)

Question: Draw a stepwise, detailed mechanism for the following reaction.

Short Answer

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Answer

Step by step solution

[4+2] cycloaddition reaction

The electrocyclic addition reaction between a four-pi system (diene) and a two-pi system (dienophile) is referred to as the [4+2] cycloaddition reaction.

All [4+2] cycloaddition reactions are thermally feasible.

Mechanism

The mechanism of the given reaction is shown below.

Mechanism

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Most popular questions from this chapter

Question: Using the Woodward–Hoffmann rules in Table 27.4, predict the stereochemistry of each reaction.

a. a [6 + 4] thermal cycloaddition

b. photochemical electrocyclic ring closure of deca-1,3,5,7,9-pentaene

c. a [4 + 4] photochemical cycloaddition

d. a thermal [5,5] sigmatropic rearrangement

Question: (a) What product is formed by the Claisen rearrangement of compound Z? (b) Using what you have learned about ring-closing metathesis in Chapter 26, draw the product formed when the product in part (a) is treated with Grubbs catalyst. These two reactions are key steps in the synthesis of garsubellin A, a biologically active natural product that stimulates the synthesis of the neurotransmitter acetylcholine. Compounds of this sort may prove to be useful drugs for the treatment of neurodegenerative diseases such as Alzheimer’s disease.