Orientation and Relative Reaction Rate Factors in Aromatic Substitution by the Benzenesulfonimido Radical

Heacock, J. F.; Edmison, M. T.

doi:10.1021/ja01498a056

Cited by 37 publications

(17 citation statements)

References 18 publications

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“…The relative reactivities of the substituted benzenes compared with benzene itself were determined using the competitive technique. The total rate ratios are collected in Table V and compared with the total rate ratios reported for benzenesulfonamidation (3). On the basis of these results, apparent partial rate factors can be calculated and are given in Table VI.…”

Section: Discussionmentioning

confidence: 99%

“…The decompositions were carried out a t 105-120° and the products analyzed after preliminary hydrolysis of the anilides forined (2) or as the arnides but after appreciable pretreatment (3). Of the aromatic coiiipounds studied, most of those with rneta-directing substituents did not react to produce the expected substitution products.…”

mentioning

confidence: 99%

“…radical C6H5S02N. (3). The failure of compounds with iiieta-directing substituents to produce the expected substitution products was attributed to complexing of the radical with the electron-rich substituent group (3).…”

mentioning

confidence: 99%

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The Reaction of Sulfonylimido Intermediates With Aromatic Compounds

Abramovitch¹,

Roy²,

Uma³

1965

Can. J. Chem.

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'Therlnolysis of rnethanesulfonyl azide in aromatic solvents gives tnethanesulfonarnide and the isomeric niethanesulfonanilides. The orientation of the latter and the relative reactivities of the aromatic substrate towards attack by the ~nethylsulfonylimido intermediate have been studied quantitatively. The high reactivity and also great selectivity of the attacking species are interpreted in terms of a rate-determining addition process to give a sulfonylaziridine derivative followed by a product-deterlllining ring opening and rearrangement t o the substituted anilides. Partial rate factors are discussed, as are possible mechanisms for the formation of the rnethanesuifonamide. The ~netl~anesulfonylimido intermediate must be abstracting two hydrogen atoms synchronously from the aromatic substrate.

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Section: Discussionmentioning

confidence: 99%

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confidence: 99%

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The Reaction of Sulfonylimido Intermediates With Aromatic Compounds

Abramovitch¹,

Roy²,

Uma³

1965

Can. J. Chem.

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“…The orientation and partial and total rate factors in the substitution of benzene derivatives by the benzenesulfonimido radical have been studied (98,136). The results were said to be consistent with an attack of the aromatic nucleus by the electrophilic free radical c&&So& (136). The failure of compounds with meta directing substituents to produce the expected substitution products was attributed to complexing of the radical with the electron-rich substituent group.…”

Section: LXXIImentioning

confidence: 99%

Preparation and Properties of Imido Intermediates (Imidogens)

Abramovitch¹,

Davis²

1964

Chem. Rev.

200

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“…However, attempts have been made with reagents such as hydroxyl ammonium salts, [566][567][568][569][570][571] hydroxylamine-O-sulfonic acid, 572,573 hydrazoic acid, [574][575][576] and organic azides, [577][578][579][580] mostly under Lewis acid-catalyzed conditions (and also with thermal initiation [581][582][583][584][585][586][587] or photolysis 588,589 ). However, attempts have been made with reagents such as hydroxyl ammonium salts, [566][567][568][569][570][571] hydroxylamine-O-sulfonic acid, 572,573 hydrazoic acid, [574][575][576] and organic azides, [577][578][579][580] mostly under Lewis acid-catalyzed conditions (and also with thermal initiation [581][582][583][584][585][586][587] or photolysis 588,589 ).…”

Section: Aminationmentioning

confidence: 99%