The cleavage of a silyl ether (R-O-SiR'3) is accomplished by treatment with (C4H9)4NF in the presence...
The cleavage of a silyl ether (R-O-SiR'3) is accomplished by treatment with (C4H9)4NF in the presence of a small amount of water. One product is the alcohol, R-OH. Give the complete mechanism using curved arrow formalism and show the other product which is formed.
Homework Answers
ANSWER:
- Proposed mechanism:
- Nucleophilic substituion on silyl ether by fluoride ion producing an OR- and a molecules of R'3Si-F
- The OR- ion atacks the water molecule to generate the alcohol and OH-
- The OH- reacts with R'3Si-F (formed in the first step) to produce R'3Si-OH and regenerate the F-
- General reaction
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