Dealkylation of Ethers. A Review.B.C. Ranu & S. BharOrg. Prep. Proced. Int. 28(4), 371-409 (1996)
(
https://www.thevespiary.org/rhodium/Rhodium/pdf/ether.dealkylation.review.pdf)
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IntroductionI) Dealkylation of Alkyl and Aryl Ethers1) Acidic Reagents a) Hydrobromic Acid in Presence of Phase Transfer Catalyst
b) Boron Tribromide
c) Boron Trihalide - Methyl Sulfide Complex
d) Boron Tribromide - Sodium Iodide - 15-crown-5
e) Dimethylboron Bromide
f) Boron Triiodide-N.N-Diethylaniline Complex
2) Basic Reagentsa) Sodium Salt of N-Methylaniline
b) Sodium Ethanethiolate
c) Sodium Benzylselenoate
3) Miscellaneous Reagentsa) Trimethylsilyl Iodide
b) Chlorotrimethylsilane und Acetic Anhydride
c) Zinc and Acyl Chloride
d) Lithium Chloride in DMF
e) Potassium in THF - A Reductive Cleavage Agent
f) Low Valent Titanium in THF - A Reductive Dealkoxylation
g) Metallic Nitrate Supported on Silica Gel - An Oxidative Cleavage Reaction
h) Nitrogen Dioxide - An Oxidative Cleavage Reagent
II) Dealkylation Of Allyl And Benzyl Ethersa) Aluminium Chloride - N,N-Dimethylaniline
b) Cationic Iridium Complex
c) Samarium(III)Chloride-Catalyzed Electrolysis
d) Low Valent Titanium
e) Zirconocene Dichloride -
n-BuLi
f) PdCl
2 - CuCl - DMF - H
2O - O
2g) Pd(Ph
3)
4 - NaBH
4h) N-Bromosuccinimide
i) Boron Trichloride - Methyl Sulfide Complex
III) Cleavage Of Cyclic Ethersa) Palladium(II)Complexes in Presence of Organotin Halides
b) Sodium Iodide - Acyl Chloride
c) Platinum Complexes
d) Aluminum Chloride - Sodium Iodide - Acetonitrile
e) Zinc - Acyl Chloride
f) Trimethylsilyl Iodide
IV) Selectivity in Dealkylation Of Ethers a) Selective Dealkylation of Alkyl Ether
b) Selective Dealkylation of Aryl Ether
c) Selective Dealkylation of Allyl Ether
a) Selective Dealkylation of Benzyl Ether
V) ConclusionVI) References