SOME REACTIONS OF 1,3-DICHLORO-2-AZONIAALLENE SALTS WITH HETERONUCLEOPHILES

1,3-Dichloro-2-azoniaallene hexachloroantimonates (1) reacted with H2S to give 1,2,4-dithiazolium salts 2. With hydrazines 1,2,4-triazolium salts (3, 4) were formed. 1,3-Dimethylurea, respectively 1,3-dimethylt hiourea or ethyl allophanate, reacted with 1 to afford 2-oxo- or 2-thi oxo-1,3,5-triazinium salts (5-7). With diphenylmethaneimines imino sub stituted 2-azoniaallene salts 8 were produced. From chloroacetonitrile dichloropyrimidines 9, and from the tricyanomethyl anion a hexatriene 10 and a triazine 11 could be prepared. The 1,5-dichloro substituted 2-azoniaallene salts 12 reacted as bifunctional electrophiles with nuc leophiles such as benzophenone hydrazone or anilines, to furnish 1,3,5 -triazinium salts 14. Against benzohydrazide the allene 12j behaved as trivalent electrophile giving the bicyclic 1,3,5-oxadiazinium salt 13 j, the constitution of which has been secured by a crystal structural analysis. The vinyl-2-azoniaallene salt ii cyclized on heating to the 1,3-thiazinium salts 16, 17. From 17 the triazinium salts 18 were prep ared with alcohols.