Tert-Butyl hypochlorite

If a bromomethyl- or vinyl-substituted cyclopropane carbon atom bears a hydroxy group, the homoallyiic rearrangement leads preferentially to cyclobutanone derivatives (J. Sa-laun, 1974). Addition of amines to cydopropanone (N. J. Turro, 1966) yields S-lactams after successive treatment with tert-butyl hypochlorite and silver(I) salts (H.H. Wasserman, 1975). For intramolecular cyclopropane formation see section 1.16. 

Ammonium sulfate triolein, oleic acid, androsten-3,17-dione, xanthanonic acid, cholesterol-propionate, N-methy Ipheny lalanine, D-glucose fluorescence after heating to 150 — 180 °C, exposure to tert-butyl hypochlorite [203]... 

Dipping solution I may be stored in the refrigerator for a few days. tert-Butyl hypochlorite should be stored cool in the dark under an atmosphere of nitrogen. 

Fluoroalkyl selenides are oxidized to higher oxidation states by tert-butyl hypochlorite under the mild conditions [115] (equation 105)... 

The amine hydrogens of polyfluorinated anilines can be replaced with chlorine by using tert-butyl hypochlorite [65,66]... 

The sulfur analogue of the Hauser ortho-substitution rearrangement provides access to an arylacet-ic NSAID. Reaction of the aminobenzophenone 176 with ethyl methylthioacetate and tert-butyl hypochlorite gives the intermediate 178. The reaction probably proceeds by way of formation of the S-chlorinated sulfonium derivative 177 displacement on sulfur will lead to the salt 178. Treatment with triethylamine leads initially to the betaine 179. Electrocyelic rearrangement of that transient intermediate leads, after rearomatization, to the homoanthranilic acid 180. Internal ester-amine interchange leads then to indolone 181 [45]. The thiomethyl group is then removed with Raney niekel. Saponifieation of intermediate 182 affords bromfenac (183) [46J. 

A) The preparation of [H-chloroethoxyjchloromethyl]phosphonic acid Acetaldehyde (1.1 mol) and hydroxymethylphosphonlc acid (1 mol) in 500 ml of benzene are saturated with hydrogen chloride gas at 10°C to 15°C. The mixture is aged at 25°C for 24 hr, the solvent distilled out in vacuo and the residue flushed three times with benzene to remove all traces of hydrogen chloride. The residue is taken up in benzene (500 ml), treated with tert-butyl hypochlorite (0.8 mol) and azobisisobutyronitrile (0.8 mm) at 40°C until titration shows the absence of hypochlorite and the solution is then evaporated to yield [(1-chloro-ethoxy)chloromethyll phosphonic acid in the form of an oil. 

Acridine-9-carbaldehyde (24%) is one of several products formed from the oxidation of 5//-dibenz[A/]azepine with tert-butyl hypochlorite in dichloromethane at — 70 C.229 The reaction is even more complex in the presence of silver(I) trifluoroacetate, and an analysis of the reaction mixture by GC-MS techniques reveals the presence of eleven products, the major ones being acridine (37%), an unidentified 5//-dibenz[/ ,/]azepinecarbaldehyde (23%) and acridine-9-carbaldehyde (9 %). 

Treatment with two equivalents of tert-butyl hypochlorite and subsequent reduction with sodium/naphthalene. 

Chloroanthracene has been prepared by the action of chlorine,2 tert-butyl hypochlorite, l,3-dichloro-5,5-dimethylhy-dantoin, or phosphorus pentachloride 5 on anthracene. 

Spray solution 1 Mix 1 ml tert-butyl hypochlorite with 100 ml cyclohexane. 

Spray solution 1 tert-Butyl hypochlorite solution. 

The chromatogram is freed from mobile phase in the drying cupboard (10 min 160 °C) and placed while still hot in the chamber with tert-butyl hypochlorite vapor for 5 min. After removal of excess reagent (15 min stream of warm air) the chromatogram is sprayed with reagent 2. 

Butane, 1,4-diiodo-, 30, 33 2-Butanone, 3-acetamido-, 33,1 n-BuTYLACETYLENE, 30, IS tert-Butyl alcohol, 30, 19, 20 32, 20 ierl-Butylbenzene, 32, 91 n-Butyl bromide, 30, 16 tert-Butyl hypochlorite, 32, 20 n-Butyl iodide, 30, 34 Butylketene dimer, 31, 71 -ter -Butylphenyl salicylate, 32, 26 Butyrchloral, 33, IS Butyric acid, a, y-dicyano-o-phenyl-, ethyl ester, 30, 80... 

Hutchins, M. G. K. et al., Tetrahedron Lett., 1981, 22, 4599-4602 Interaction of sodium hydrogen cyanamide and tert-butyl hypochlorite in methanol at —50°C to ambient temperature forms cyanonitrene. Isolation gave an orange dimeric residue which exploded on two occasions. 

Oxidation by chlorine to the arylimidosulfonyl chlorides is sometimes violent, and tert-butyl hypochlorite is a milder reagent. 

Chlorination of yohimbine (74) at the (3 position of the indole moiety with tert-butyl hypochlorite and treatment of the resulting chloride (539) with base in... 

In a 50 mL round-bottomed flask equipped with a magnetic stirrer bar were placed tert-butyl carbamate (545 mg) and n-propanol (6 mL). A solution of sodium hydroxide (183 mg) in water (12.2 mL) and tert-butyl hypochlorite (0.53 mL) were added to the solution. The resulting solution was stirred for 5 minutes and cooled to 0°C. Then a solution of DHQ2PHAL (71 mg) in n-propanol (6mL), a solution of 4-methoxystyrene in //-propanol (12.2 mL) and potassium osmate dihydrate (22.5 mg) were added sequentially to give a green solution. After 1 hour at 0 °C, the reaction mixture had turned from green to yellow. 

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