Chloramine imidation with

Treatment of sterically-crowded selones possessing substituted bornane skeletons with chloramine-T afford several products derived from intermediary selone Se-imides (Scheme 37). Direct observation of the intermediates was done by NMR monitoring at low temperature.240... 

The yield of amino alcohols has been shown to improve by addition of tertiary alkyl bulkhead amines, and catalytic cycles using chloramine-T (364, 366, 367) or IV-chloro-lV-argentocarbamates (368) have been devised. By the use of asymmetric inductants such as (-)-10,11-dihydro-quinine with the imide, optically active amino alcohols have been produced (369). 

As indicated by structures (64) and (65), the method was also employed for the -imidation of jS-lactam sulphides, including transformations of penicillins, which reacted with two mole equivalents of Chloramine-T. 

Selenium di-imides (132) were formed in methylene chloride solution from selenium tetrachloride with t-butylamine or sulphonamides and also from selenium metal with anhydrous Chloramine-T. They were found to be efficient reagents for the allylic amination of alken and alkynes. The first examples of selenium imides (133) were synthesized from diaryl selenides and Chloramine-T, from... 

The synthesis of allyl sulfonamides by imidation of allyl sulfides with chloramine-T (TsNClNa) and subsequent [2,3]-sigmatropic rearrangement has been reported (Scheme 43). ... 

Sulphimides.—(S)-(-)-2-Carboxyphenyl methyl N-toluene-p-sulphonyl sul-phimide (68 2-carboxyphenyl in place of Tol) may be prepared by the reaction of the corresponding sulphide with Chloramine-T, foUowed by conventional resolution, or from the optically active sulphoxide by reaction with NN -bis(toluene-p-sulphonyl)sulphur di-imide. " Acid-catalysed hydrolysis gives the sulphoxide with retention of configuration, and an-chimeric assistance by carboxylate is demonstrated, as for reactions of the sulphoxide itself. " (R)-(+)-Methyl-p-tolyl sulphoxide reacts with tol-uene-p-sulphonyl isocyanate to give the corresponding N-toluene-p-sulphonyl sulphimide (68) with net inversion, though product and recovered sulphoxide are partly racemized. The same sulphoxide reacts with toluene-... 

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