2Me hv .CO2Et RT "CO,Me Ar ELOH R Ar 2 Ar- CO2ET 1 R. CO,Me R. CO,Me CF3SO3H CH2CI2, A RT CO2M CO2ME Ar = 3,4,5-trimethoxyphenyl R= OMe R Ar 3 R 4

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 11.37P: Following are the steps in the industrial synthesis of glycerin. Provide structures for all...
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2. The cyclization of E,E-dibenzylidenesuccinate esters to dihydronaphthalenes has been
employed as the key step in the synthesis of lignins.
.CO,Me
hv
CO2Et
"CO,Me
Ar
ELOH
Ar
Ar
CO2ET
R.
.CO,Me
R.
CO2M.
CF3SO3H
CH,Cl2, A
+
'CO,Me
Är
3
RT
CO,Me
Ar = 3,4,5-trimethoxyphenyl
R = OMe
a. Propose a reasonable mechanism for the cyclcilzation processes and justify the
stereochemistry of dihydronaphthalenes 2 and 3.
b. Suggest a mechanism for the formation of 4.
2.
Transcribed Image Text:2. The cyclization of E,E-dibenzylidenesuccinate esters to dihydronaphthalenes has been employed as the key step in the synthesis of lignins. .CO,Me hv CO2Et "CO,Me Ar ELOH Ar Ar CO2ET R. .CO,Me R. CO2M. CF3SO3H CH,Cl2, A + 'CO,Me Är 3 RT CO,Me Ar = 3,4,5-trimethoxyphenyl R = OMe a. Propose a reasonable mechanism for the cyclcilzation processes and justify the stereochemistry of dihydronaphthalenes 2 and 3. b. Suggest a mechanism for the formation of 4. 2.
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