The nitrogen-sulfur linkage in compounds of the type R-NSO is capable of undergoing addition. For N-sulfinylsulfonamides in particular, the reactivity is increased so greatly that new types of compounds may be obtained by cyclic addition or migration of the sulfinyl group.In 1890, Michaelis and Herz [l) identified "thionylaniline" C~HSNSO as a product of the reaction of aniline with SOC4:(1) QHsNHz + SOClz + GHsNSO + 2 HCL This substance has been described earlier by Bottinger [2] but with no statement concerning its structure. In a large number of subsequent publications, Michaelis has described the preparation of approximately seventy-five N-sulfinylamines of the type R-NSO and their reactions. This thorough exploration of the field, as well as the fact that the described reactions either led back to the amines, or else to products which could be obtained more easily by another route, explains why very little work was done with the N-sulfinyl compounds in the subsequent period. Only in the last few years have various groups made renewed studies of the structure and behavior of the organic N-sulfinyl compounds, and it is these studies in particular which are described here. The literature up to June 1958 is summarized in Houben-Weyl [3a] and is therefore only treated briefly; a survey of earlier works is also given by Kennard [3 b]. A summary of the properties of the unsubstituted thionylimide has been given by Goehring [4].Most N-sulhyl compounds known up to the present time are amine or bydrazine derivatives and are prepared from them.

Cycloadditions and other reactions of compounds containing the groups NSO and NSN are reviewed.

Zwei neue Wege zu N-Arylsulfonyl-iminen bzw. -formamidinen werden beschrieben. Im Rahmen unserer Arbeiten iiber Diensynthesen, die zu Heterocyclen fiihren, haben wir uns auch mit den Sulfonyliminen RSOzN=CHR beschtiftigt, da diese a h C =N-Dienophile von Inter-sein konnen. Diese Schiffschen Basen von Sulfonamiden sind seit einigen Jahren bekannt. J. LICHTEN-BERGER und Mitarbb.1) bzw. A. J. KRETOW und JE. A. ABRASHANOWA~) erreichten die Kondensation von Arylsulfonamiden mit Aldehyden mit AlCl3 bzw. ZnClz als Kondensationsmittel.

No abstract

No abstract