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Chapter 26: Q 29. (page 1070)

What ring-closing metathesis product is formed when each substrate is treated with Grubbs catalyst under high-dilution conditions?

a.

b.

c.

Short Answer

Expert verified

Answer

Product of b

Step by step solution

01

Ring-closing metathesis

Under the reactions of olefinic metathesis, the intramolecular metathesis of the terminal alkenes that form multiple unsaturated rings is called ring-forming metathesis. The cycloalkenes formed are E and Z isomers.

02

Grubbs catalyst

The series of the transition metal carbenes used especially for olefinic metathesis are the Grubbs catalysts.

03

Products of the given reaction

Under high-dilution conditions, the Grubbs catalyst favors the intramolecular ring-closing metathesis.

a. A six-membered ring is formed by the intramolecular metathesis. The product is shown below.


Product of a

b. A six-membered ring is formed by the intramolecular metathesis. The product is shown below.

Product of b

c. A five-membered ring is formed by the intramolecular metathesis. The product is shown below.

Product of c

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Most popular questions from this chapter

Sulfur ylides, like the phosphorus ylides of Chapter 21, are useful intermediates in organic synthesis. Methyl trans-chrysanthemate, an intermediate in the synthesis of the insecticide pyrethrin I (Section 26.4), can be prepared from diene A and a sulfur ylide. Draw a stepwise mechanism for this reaction.

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Draw the products (including stereoisomers) formed in each reaction.

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