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Chemistry / Organic Chemistry 8 / Chapter 18 / Problem 14P

Organic Chemistry | 8th Edition | ISBN: 9780321768414 | Authors: L.G. Wade Jr

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Like other strong nucleophiles, triphenylphosphine attacks

Chapter 12, Problem 14P

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QUESTION:

Problem 14P

Like other strong nucleophiles, triphenylphosphine attacks and opens epoxides. The initial product (a betaine) quickly cyclizes to an oxaphosphetane that collapses to an alkene and triphenylphosphine oxide.

(a) Show each step in the reaction of trans-2,3-epoxybutane with triphenylphosphine to give but-2-ene. What is the stereochemistry of the double bond in the product?

(b) Show how this sequence might be used to convert cis-cyclooctene to trans-cyclooctene.

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QUESTION:

Problem 14P

Like other strong nucleophiles, triphenylphosphine attacks and opens epoxides. The initial product (a betaine) quickly cyclizes to an oxaphosphetane that collapses to an alkene and triphenylphosphine oxide.

(a) Show each step in the reaction of trans-2,3-epoxybutane with triphenylphosphine to give but-2-ene. What is the stereochemistry of the double bond in the product?

(b) Show how this sequence might be used to convert cis-cyclooctene to trans-cyclooctene.

ANSWER:

Solution 14P

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