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Chapter 30: Q.30-9 (page 1030)

When a 2,6-disubstituted allyl phenyl ether is heated in an attempted Claisen rearrangement, migration occurs to give the p-allyl product as the result oftwo sequential pericyclic reactions. Explain.

Short Answer

Expert verified

The product is formed by Claisen rearrangement which is followed by Cope rearrangement. This involves [3,3] sigmatropic reaction, it also follows enolization

Step by step solution

01

It involoves two pericyclic reactions.

The overall reaction given below follows 2 pericyclic reactions

02

The overall mechanism involve[3,3] sigmatropic reaction.

The product is formed by Claisen rearrangement which is followed byCope rearrangement. This involves [3,3] sigmatropic reaction, it also follows enolization. (As shown in the figure below).

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Most popular questions from this chapter

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Answer Problem 30-22 for the thermal and photochemical cyclizations of (2E,4Z,6Z,8Z)-2,4,6,8-decatetraene.

What product would you expect to obtain from the photochemical cyclizationof (2E,4Z,6E)-2,4,6-octatriene? Of (2E,4Z,6Z)-2,4,6-octatriene?

What stereochemistry鈥攁ntarafacial or suprafacial鈥攚ould you expect to observe in the following reactions?

(a) A photochemical [1,5] sigmatropic rearrangement

(b) A thermal [4 + 6] cycloaddition

(c) A thermal [1,7] sigmatropic rearrangement

(d) A photochemical [2 + 6] cycloaddition
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