2-Chloro-1-(chloromethyl)ethyl methoxymethyl ether as a reagent for acetonylation of alcohols and phenol

Gu, Xue Ping; Ikeda, Isao; Komada, S.; Masuyama, Araki; Okahara, Mitsuo

doi:10.1021/jo00376a074

Cited by 9 publications

(2 citation statements)

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“…IR (film): ν = 2976 cm -1 , 1722, 1471, 1422, 1391, 1367, 1237, 1193, 1106, 883. 1 H-NMR (CDCl 3 , 250 MHz): δ = 1.22 (s, 9 H), 2.17 (s, 3 H), 3.94 (s, 2 H) 48.…”

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confidence: 99%

Photooxidative Damage of Guanine in DG and DNA by the Radicals Derived from the α Cleavage of the Electronically Excited Carbonyl Products Generated in the Thermolysis of Alkoxymethyl-Substituted Dioxetanes and the Photolysis of Alkoxyacetones

2000

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On thermolysis of the methoxy (MeO-TMD), tert-butoxy (tBuO-TMD), and hydroxy (HO-TMD) derivatives of 3,3,4,4-tetramethyl-1,2-dioxetane (TMD) in the presence of dG and calf-thymus DNA, the guanine is oxidized considerably more efficiently than the parent TMD. The same trend in the oxidative reactivity is observed for the photolysis of the corresponding oxy-substituted ketones versus acetone. The oxidative reactivity order in the dioxetane thermolysis, as well as in the ketone photolysis, parallels the ability of the excited ketones to release radicals (determined by spin trapping with DMPO and EPR spectroscopy) upon alpha cleavage (Norrish-type-I reaction). In the presence of molecular oxygen, the carbon-centered radicals are scavenged to produce peroxyl radicals, which are proposed as the reactive species in the oxidation of the guanine in dG and calf-thymus DNA.

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“…IR (film): ν = 2976 cm -1 , 1722, 1471, 1422, 1391, 1367, 1237, 1193, 1106, 883. 1 H-NMR (CDCl 3 , 250 MHz): δ = 1.22 (s, 9 H), 2.17 (s, 3 H), 3.94 (s, 2 H) 48.…”

mentioning

confidence: 99%

Photooxidative Damage of Guanine in DG and DNA by the Radicals Derived from the α Cleavage of the Electronically Excited Carbonyl Products Generated in the Thermolysis of Alkoxymethyl-Substituted Dioxetanes and the Photolysis of Alkoxyacetones

2000

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“…One published (26) method for the preparation of 1-alkoxy-2-propanone is based on the reaction of an alcohol with 2-chloro-l-(chloromethyl) ethyl methoxymethyl ether under alkaline conditions in dioxane and then by acidic hydrolysis (26).…”

Section: Rearrangement Reactionmentioning

confidence: 99%

The alkyl glycidyl ether as synthetic building blocks

Urata

Takaishi

1994

J Americ Oil Chem Soc

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Alkyl glycidyl ether is one of the most useful key materials for industrial applications because the addition reaction of various kinds of nucleophilic reagents to the reactive epoxy bond of the glycidyl ethers has led to glyceryl ether derivatives. Glyceryl ether exhibits many interesting physical and pharmacological properties. The alkyl glycidyl ether can presently be produced at an industrial scale under the phase-transfer catalytic Williamson ether synthesis. We have reviewed some addition reactions of the alkyl glycidyl ether and possibilities for use as the building blocks for the syntheses of surfactants, pharmaceuticals, etc. that contain glyceryl ether skeletons. Typical examples of alkyl glyceryl ether derivatives include: amino ether as cosmetic material, and isodiglycerin mono-and dialkyl ethers and triglycerin monoalkyl ether as a cosmetic or a pharmacologically useful material, respectively. Another interesting reaction is the rearrangement of the epoxy bond of the alkyl glycidyl ether, which gives alkoxy ketone in a one-pot synthesis. KEY WORDS: Addition reactions, alkoxy ketone, glyceryl ether, glyceryl ether derivatives, glycidyl ether, isodiglycerin dialkyl ether, isodiglycerin monoalkyl ether, phase-transfer catalytic Williamson ether synthesis, triglycerin monoalkyl ether.

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Preparation of Difunctional Compounds

1988

Compendium of Organic Synthetic Methods

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2-Chloro-1-(chloromethyl)ethyl methoxymethyl ether as a reagent for acetonylation of alcohols and phenol

Cited by 9 publications

References 0 publications

Photooxidative Damage of Guanine in DG and DNA by the Radicals Derived from the α Cleavage of the Electronically Excited Carbonyl Products Generated in the Thermolysis of Alkoxymethyl-Substituted Dioxetanes and the Photolysis of Alkoxyacetones

Photooxidative Damage of Guanine in DG and DNA by the Radicals Derived from the α Cleavage of the Electronically Excited Carbonyl Products Generated in the Thermolysis of Alkoxymethyl-Substituted Dioxetanes and the Photolysis of Alkoxyacetones

The alkyl glycidyl ether as synthetic building blocks

Preparation of Difunctional Compounds

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