1-Chlorobenzotriazole, oxidation

Aldoximes can be oxidatively dehydrogenated to nitrile oxides using a variety of oxidants such as lead tetraacetate [16a], alkali hypohalites [lla],NBS in DMF followed by base treatment [16b], chloramine-T [11b], 1-chlorobenzotriazole [16c], mercuric acetate [ 16 d], etc. However, we employed either NaOCl or chloramine-T for most of our INOC reactions. For instance, a piperidine ring fused to an isoxazoline as in 14 was constructed using the INOC methodology (Scheme 3) [17]. Monoalkylation of N-tosylallylamine 10 with the bromoacetal... 

A simple but accurate potentiometric method for the estimation of mercaptans in 0.01 M perchloric acid is based on their quantitative oxidation to disulfide with 1-chlorobenzotriazole. A backtitration procedure can also be used <90Mi40l-03>. 

Diammonium hexanitratocerate (IV) (CAN) has also been used as an oxidizing agent for aldoximes. This approach is especially useful for the preparation of ahphatic 2-oxo-carbonitrile oxides (99). Another useful reagent for the generation of nitrile oxides from aldoximes is 1-chlorobenzotriazole (100). Due to its reactivity toward both aldoximes and olefins, this reagent can only be used to prepare stable... 

Secondary alkyl ethers can be oxidized to ketones by bromine (e,g., Me2CHOCHMe2 + Br — Me2CO).109 Primary alkyl ethers give carboxylic acids (9-22) with bromine, but can be cleaved to aldehydes with l-chlorobenzotriazole.lln... 

Benzotriazole can be chlorinated at the N(l) position by NaOCl (85H(23)2225). 1-Chlorobenzotriazole - a rather stable crystalline compound that has found application in organic synthesis as a selective chlorinating reagent and mild oxidant. A-Fluorination of benzotriazole with cesium fluoroxysulfate gives 1-fluorobenzotriazole in 25% yield (91T7447). 

Oxidation of phenothiazines with 1-chlorobenzotriazole followed a first-order dependence on the oxidant and a zero-order dependence on the reductant concentration. Hypochlorous acid has been suggested as the rective oxidizing species. A mechanism consistent with the observed results has been proposed.155... 

Several medio are available for the intnxluction of sulfenyl groups a to carbonyl derivatives and these have been reviewed. - The most versatile procedure involves reaction of the enolate with an appropriate thiol derivative, but the preferred m od is largely dependent on the nature of the substrate employed (see below). In most instances, sulfur has been introduced in the divalent state and subsequently oxidized, although the oxidative step has been avoided by the direct introduction of sulfur at the S oxidation level. The oxidation of sulfides to sulfoxides is a trivial procedure that can be effected by a variety of reagents. Sodium metaperiodate, m-chloroperbenzoic acid and hydrogen peroxide are the most common oxidants, but r-butyl hydroperoxide, r-butyl hypochlorite, N-chlorobenzotriazole,... 

OXIDATION, REAGENTS Dimethylsulf-oxide-Acetic anhydride. 1-Amyl hydroperoxide. N-Bromosuccinimide. Ceric ammonium nitrate. Chloramine. o-Chlo-ranil. 1-Chlorobenzotriazole. N-Chloro-succinimide-Dimethyl Sulfide. Chromic acid. Chromic anhydride. Chromyl chloride. Cobalt(ll) acetate. Cupric acetate monohydrate. Cupric nitrate-Pyridhic complex. 2,3-Dichloro-5,6-dicyano-l, 4-benzoquinonc. Dicyclohcxyl-18-crown-... 

Johnson, C. R., Bacon, C. C., Kingsbury, W. D. Chemistry of sulfoxides and related compounds. XXXVIII. Oxidation of sulfides with 1-chlorobenzotriazole. Preparation of amino- and alkoxysulfonium salts. Tetrahedron Lett. 1972, 501-503. 

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