TL;DR: The scope and limitations of reagents for the cleavage of ethers are discussed in this paper, where the reagents are conveniently classified in the five main headings: basic reagents 3.1. Bronsted Acids 2.2. Lewis Acids 3.3. Alkali Metals 3.4.
Abstract: The scope and limitations of reagents for the cleavage of ethers are discussed. The reagents are conveniently classified in the five main headings. Selectivity patterns of some of the reagents are discussed in cases where sufficient data has been given in the literature. 1. Introduction 2. Acidic Reagents 2.1. Bronsted Acids 2.2. Lewis Acids 3. Basic Reagents 3.1. Alkali Hydroxides 3.2. Alkali Alkoxides 3.3. Alkali Amides 3.4. Alkali Metals 3.5. Organo-Alkali Metal Compounds 3.6. Sodium Cyanide/Dimethyl Sulfoxide 3.7. Sodium Ethanethiolate 3.8. Sodium Thiocresolate 3.9. Lithium Iodide 3.10. Sodium Benzeneselenolate 4. Miscellaneous Reagents 4.1. Iodotrimethylsilane 4.2. Iodotrichlorosilane 4.3. Dichloroiodomethylsilane 4.4. Bromotrimethylsilane 4.5. Alkylthiotrimethylsilanes 4.6. Ethanethiol or Ethanedithiol/Boron Trifluoride Etherate 4.7. Aluminium Halide/Thiol Systems 4.8. Acetyl Iodide and Pivaloyl Iodide 4.9. Diiodomethyl Ether/Hydrogen Iodide 5. Reductive Cleavage of Ethers 5.1. Lithium Tris[t-butoxy]aluminium Hydride/Triethylborane Complex 5.2. Hydrogenolysis 6. Oxidative Cleavage of Ethers 6.1. Ceric Ammonium Nitrate 6.2. Silver Oxide 6.3. Dichlorodicyanoquinone 6.4. Tris[p-bromophenyl]ammonium Hexachloroantimonate 7. Photochemical Cleavage of Ethers 8. Selectivity in Ether Cleavage 8.1. Stereoelectronic Characteristics of the Ether-Cleaving Agent 8.2. Structural Features of the Groups Cleaved 8.3. Molecular Environment of the C-O Bond not Undergoing Cleavage 9. Addendum
TL;DR: In this paper, a photofragment spectroscopy of acetyl iodide (CH3COI) at 266 nm shows evidence of a two-step dissociation into three products.
Abstract: Photofragment spectroscopy of acetyl iodide (CH3COI) at 266 nm shows evidence of a two‐step dissociation into three products. Initial photodissociation yields an iodine atom and a highly internally excited acetyl radical containing on average 80% of the energy available in the dissociation process. The transition dipole moment of the initial absorption lies in the C–C–O plane near the C–I bond axis, and breakup of the photoexcited acetyl iodide is rapid, on the order of 10−13 sec. The acetyl fragment is found to live for several rotational periods, ∼10−11 sec. Its subsequent decomposition to CO and CH3 can be modeled by statistical theories of unimolecular decay. It is found that an average 30% of the energy residing in the acetyl radical ultimately appears as relative translational energy of the CO and CH3 fragments.
TL;DR: In this paper, the cationic ring-opening polymerization of 2-ethyl-2-oxazoline was conducted using acetyl chloride, acetyl bromide, and acetyl iodide as initiators.
Abstract: Kinetic investigations on the cationic ring-opening polymerization of 2-ethyl-2-oxazoline were conducted using acetyl chloride, acetyl bromide, and acetyl iodide as initiators. Various polymerization temperatures ranging from 80 to 220 °C were applied under microwave irradiation. The resulting polymerization mixtures were characterized with GC and GPC for the determination of monomer conversion and molecular weight distribution, respectively. Well defined polymers with narrow molecular weight distributions ( = 6 000 Dalton, PDI ≈ 1.10) were obtained with all three initiators.
TL;DR: In this article, rare earth metal iodides having the general formula LnI3·8DMF (Ln = La, Pr Nd, Sm, or Gd; DMF = N:N′-dimethylformamide) have been prepared by reaction of the hydrated acetate with acetyl iodide in dimethyl formamide or by metathesis between the anhydrous chloride and potassium iodide, in the same solvent.
TL;DR: In this article, the infrared spectra of [2H3]acetyl chloride, acetyl bromide, and acetyl iodide have been obtained in both the liquid and gaseous phase and frequencies have been assigned to the fundamental vibrations.
Abstract: The infrared spectra of acetyl fluoride, acetyl chloride, [2H3]acetyl chloride, acetyl bromide, and acetyl iodide have been obtained in both the liquid and gaseous phase and frequencies have been assigned to the fundamental vibrations. The assignment for acetyl chloride is in close agreement with that of Overend et al.The low frequency values associated with the carbon–halogen stretching modes and the high ones associated with ν(CO) are attributed mainly to vibrational coupling.