Preparation and properties of selenium imides.

Abstract

Tricoordinate tetravalent sulronlum ylides, sulfonlum rmldes and sulfoxides are rsoelectronic to each other around the central sulfur atoms and their chemical and physrcal propertres have been extensively investigated during the past 10 years. 2) Meanwhrle, among the correspondrng selenium analogs the selenoxlde and the selenrum yl~de have been syntheslzed and their physrcal and chemrcal features have been partly characterized, the former berng reported for the frrst trme rn 1896,3) while the latter being prepared very recently. 4) However, the synthesis of the corresponding nrtrogen analogs, selenrum rmldes, has never been attempted so far, despite of their Inherently rnterestrng nature. In thus communication we wish to report the syntheses and an Interesting chemical behavior of a few selenrum amides. An equimolar mixture of dibenzyl selenide and tert-butyl hypochlorite was treated in CH3CN at -3OOC with an equimolar amount of solid N-sodio-ptoluenesulfonamide. After 2 hr the reaction was found to be complete as the sodium salt of the sulfonamide disappeared completely. The filtration of the precipitated sodium chloride and then the removal of the solvent from the filtrate afforded nearly quantitatively white crystals which were recrystallized from benzene-n-hexane (mp. 118-12OOC). Based on the elemental analysis, nmr, and ir spectra, the structure of the material are assigned to have the following formula (I); IR, 1245(S02), 1120(S02), 1080, 950, 690 cm-'. NMR, 6 2.35(s 3R), 4.28(s 4H), 7.3O(s,q 14H). Found: C, 58.90; H, 4.65;