Sodium Bis (trimethylsilyl) amide and Lithium Diisopropylamide in Deprotection of Alkyl Aryl Ethers: α-Effect of Silicon

…, FF Wong, JJ Huang, SC Tsay

Index: Hwu, Jih Ru; Wong, Fung Fuh; Huang, Jiann-Jyh; Tsay, Shwu-Chen Journal of Organic Chemistry, 1997 , vol. 62, # 12 p. 4097 - 4104

Full Text: HTML

Citation Number: 54

Abstract

Removal of methyl, benzyl, and methylene groups from alkyl aryl ethers is among the most popular deprotecting methods in organic synthesis. Alkali organoamides NaN (SiMe3) 2 and LiN (i-Pr) 2, often used as organic bases, have been developed as efficient deprotecting agents. Treatment of aryl methyl ethers with 1.5 equiv of NaN (SiMe3) 2 or LiN (i-Pr) 2 in THF and 1, 3-dimethyl-2-imidazolidinone in a sealed tube at 185° C produced the ...

 Related Synthetic Route
1,2-Dimethoxybenzene Structure

91-16-7

1,2-Dimethoxybenzene

~96%

1,2-Benzenediol Structure

120-80-9

1,2-Benzenediol

1,3-Benzodioxole Structure

274-09-9

1,3-Benzodioxole

~98%

1,2-Benzenediol Structure

120-80-9

1,2-Benzenediol

5-tert-butyl-1,3-benzodioxole Structure

7228-36-6

5-tert-butyl-1,...

~94%

4-tert-Butylcatechol Structure

98-29-3

4-tert-Butylcatechol

4-tert-butyl-1,2-dimethoxybenzene Structure

41280-64-2

4-tert-butyl-1,...

~93%

4-tert-Butylcatechol Structure

98-29-3

4-tert-Butylcatechol

Benzene,1-methoxy-4-phenoxy- Structure

1655-69-2

Benzene,1-metho...

~85%

4-Phenoxyphenol Structure

831-82-3

4-Phenoxyphenol

4-Ethyl-1,2-dimethoxybenzene Structure

5888-51-7

4-Ethyl-1,2-dim...

~50%

4-Ethyl-2-methoxyphenol Structure

2785-89-9

4-Ethyl-2-metho...

2-Methoxy-5-ethylphenol Structure

2785-88-8

2-Methoxy-5-eth...

3,4-Methylenedioxytoluene Structure

7145-99-5

3,4-Methylenedi...

~99%

4-methylcatechol Structure

452-86-8

4-methylcatechol

2-Methoxybenzonitrile Structure

6609-56-9

2-Methoxybenzon...

~91%

2-Cyanophenol Structure

611-20-1

2-Cyanophenol

4-Ethyl-1,2-dimethoxybenzene Structure

5888-51-7

4-Ethyl-1,2-dim...

~97%

4-ethylcatechol Structure

1124-39-6

4-ethylcatechol

2,4-Dimethoxybenzonitrile Structure

4107-65-7

2,4-Dimethoxybe...

~89%

4-hydroxy-2-methoxybenzonitrile Structure

84224-29-3

4-hydroxy-2-met...

4-Ethyl-1,2-dimethoxybenzene Structure

5888-51-7

4-Ethyl-1,2-dim...

~37%

4-Ethyl-2-methoxyphenol Structure

2785-89-9

4-Ethyl-2-metho...

2-Methoxy-5-ethylphenol Structure

2785-88-8

2-Methoxy-5-eth...

1,3-Dimethoxybenzene Structure

151-10-0

1,3-Dimethoxybenzene

~97%

m-Methoxyphenol Structure

150-19-6

m-Methoxyphenol


Home | MSDS/SDS Database Search | Journals | Product Classification | Biologically Active Compounds | Selling Leads | About Us | Disclaimer

Copyright © 2024 ChemSrc All Rights Reserved