Like other strong nucleophiles, triphenylphosphine attacks and opens epoxides. Theinitial product (a betaine) quickly cyclizes to an oxaphosphetane that collapses to analkene and triphenylphosphine oxide.(a) Show each step in the reaction of trans-2,3-epoxybutane with triphenylphosphine togive but-2-ene. What is the stereochemistry of the double bond in the product?

Organic Chemistry
8th Edition
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Chapter11: Ethers, Epoxides, And Sulfides
Section: Chapter Questions
Problem 11.26P: Acid-catalyzed hydrolysis of the following epoxide gives a trans diol. Of the two possible trans...
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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?

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