1,2-Trans-cyclohexanediol has been shown to be an efficient support for the asymmetric cyclopropanation of allylic ethers as shown in the scheme below. Ph Ph Et,Zn + CICH,I Toluene 3 h, -20°C HO. Bu,NI CH,Cl2 Ph Ph PhLi + HO. THE -100°C

Organic Chemistry
9th Edition
ISBN:9781305080485
Author:John E. McMurry
Publisher:John E. McMurry
Chapter18: Ethers And Epoxides; Thiols And Sulfides
Section18.7: Crown Ethers
Problem 15P: 15-Crown-5 and 12-crown-4 ethers complex Na+ and Li+, respectively. Make models of these crown...
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1,2-Trans-cyclohexanediol has been shown to be an efficient support for the asymmetric
cyclopropanation of allylic ethers as shown in the scheme below.
Ph
Et,Zn + CICH,I
Ph
Toluene
3 h, -20°C
OH
HO.
Bu,NI
CH2CI2
Ph
Ph
PhLi
+
но.
THF
-100°C
Transcribed Image Text:1,2-Trans-cyclohexanediol has been shown to be an efficient support for the asymmetric cyclopropanation of allylic ethers as shown in the scheme below. Ph Et,Zn + CICH,I Ph Toluene 3 h, -20°C OH HO. Bu,NI CH2CI2 Ph Ph PhLi + но. THF -100°C
(d) The final step of the reaction sequence uses PhLi.
Provide a reason and possible mechanism by which this final elimination and hydrolysis reaction
would occur.
Transcribed Image Text:(d) The final step of the reaction sequence uses PhLi. Provide a reason and possible mechanism by which this final elimination and hydrolysis reaction would occur.
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