2- -5-chlorobenzotriazole

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... 

Chloriminovanadium trichloride, 4165 A-Chloroacetamide, 0789 A-Chloroallylamine, 1202 A -Chloro-3 -aminopropyne, 1129 A -Chloro-3 -aminopropyne, 1129 1-Chloroaziridine, 0786 1-Chlorobenzotriazole, 2150 A -Chloro-bis(2-chloroethyl)amine, 1590 A-Chlorobis(trilluoromethanesulfonyl)imide, 0596 A-Chlorocinnamaldimine, 3126 A -Chlorodimethylamine, 0895 A -Chloro-4,5-dimethyltriazole, 1490 A -Chloro-4-methyl-2-imidazolinone, 1554 A -Chloro-5-methyl-2-oxazolidinone, 1488 A -Chloro-3 -morpholinone, 1489 A-Chloro-4-nitroaniline, 2231 A-Chloro-5-phenyltetrazole, 2674 A-Chloropiperidine, 1948 A -Chloropy rrolidine, 1584... 

Quite recently, an asymmetric synthesis of alkoxyaminosulfonium salt 122 and diaminosulfonium salt 125 was accomplished (163) by way of menthoxysulfonium salt 126, obtained by treating A -p-toluene-sulftnylmorphoUne with 1-chlorobenzotriazole (NCBT), followed by menthol. The subsequent addition of methanol and sodium tetra-phenylborate gave the optically active salt 122 (Scheme 7). When 126 was treated with piperidine instead of methanol, the optically active diaminosulfonium salt 125 was formed. 

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... 

A number of N-brominated and N-chlorinated heterocycles also provide sources of electrophilic bromine. Examples include 1-chlorobenzotriazole (82JOC4895 87JOC173 88CHE36) and various HBr and Br2 adducts of pyridines, or pyridine perbromides [84SC939 85JAP(K)60/87264], Polymer-supported reagents of this type include 1-cyclohexylpyridinium perbromide linked to polystyrene, effective for the bromination of 1-methylindole, benzo[fc]furan, and benzo[6]thiophene (89T7869). 

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... 

The kinetics of the chlorination of phenol and 2-naphthol by l,3-dichloro-5,5-dimethylhydantoin (2) in aqueous acidic media have been interpreted10 in terms of an initial rate-limiting formation of a charge-transfer complex between the substrate and the chlorinating agent. A kinetic study of the chlorination of nine aryl ethers by 1-chlorobenzotriazole in acetic acid has also led to mechanistic conclusions.11... 

Chlorobenzotriazole, 2143 4-Chlorobenzoyl azide, 2650 lV-Chloro-bis(2-chloroethyl)amine, 1585... 

Sulfonylbenzotriazoles 851 are readily available from reactions of benzotriazole with sulfonyl chlorides <2000JOC8210> or of 1-chlorobenzotriazole with sulfmic acids <2004JOC1849> and can be used for sulfonation of carbanions (Scheme 187) <2005JOC9191>. 

The use of acetyl nitrate in place of sulfuric-nitric mixture as a nitrating agent leads to 1-nitro derivatives [28], These compounds have also been obtained by the nitration of 1-chlorobenzotriazole with a silver nitrate complex with trimethylphos-phite [273],... 

It has already been shown that the nitration with nitric acid in acetic anhydride provides the general way of obtaining /V-ni trohctcrocyclcs. As an alternative synthesis of the aforementioned compounds, and, in particular, 1-nitrobenzotriazole, the reaction of 1-chlorobenzotriazole with the silver nitrate-triphenylphosphite complex can be suggested [273],... 

Many positive halogen compounds such as NCS," 1-chlorobenzotriazole," and chlo-... 

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