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?(b) Show how this sequence might be used to convert cis-cyclooctene to trans-cyclooctene
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?(b) Show how this sequence might be used to convert cis-cyclooctene to trans-cyclooctene
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...
Related questions
Question
Like other strong nucleophiles, triphenylphosphine attacks and opens
initial product (a betaine) quickly cyclizes to an oxaphosphetane that collapses to an
(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
Expert Solution
This question has been solved!
Explore an expertly crafted, step-by-step solution for a thorough understanding of key concepts.
This is a popular solution!
Trending now
This is a popular solution!
Step by step
Solved in 2 steps with 4 images
Knowledge Booster
Learn more about
Need a deep-dive on the concept behind this application? Look no further. Learn more about this topic, chemistry and related others by exploring similar questions and additional content below.Recommended textbooks for you
Organic Chemistry
Chemistry
ISBN:
9781305580350
Author:
William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:
Cengage Learning
Organic Chemistry
Chemistry
ISBN:
9781305580350
Author:
William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:
Cengage Learning