REACTIONS OF BIFUNCTIONAL SULFUR-COMPOUNDS WITH DIHYDRAZIDO PHOSPHORIC-ACID DERIVATIVES - 5-MEMBERED AND 6-MEMBERED RINGS WITH 4 N-ATOMS

Thionylchloride and sulfurdichloride react with N-substituted phosphor ic acid or thiophosphoric acid dihydrazides in the presence of triethy lamine to yield six-membered rings containing sulfur if the substituen ts at N adjacent to the sulfur are electron-withdrawing groups such as -C(=O)Et. These groups lacking redox reactions are observed, resultin g in the formation of a five-membered ring with an NN double bond that contains no sulfur. The X-ray structure of this ''lambda(5)-phosphate trazolin'' has been investigated: the ring is planar, PN 1.665(6), 1.6 80(6), N-N 1.372(9), 1.385(10), N=N 1.275(10)Angstrom.