80884-75-9Relevant academic research and scientific papers
5-Imino-Δ3-1,2,4-thiadiazoline Derivatives with a Linear N-S...O Grouping. Synthesis and Crystal Structures
L'abbe, Gerrit,Vermeulen, Guido,Toppet, Suzanne,King, Geoffrey S. D.,Aerts, Jozef,Sengier, Lieve
, p. 1309 - 1317 (2007/10/02)
A series of carbonyl derivatives of 5-imino-δ3-1,2,4-thiadiazolines has been prepared and shown by X-ray analysis of a selected example to have a trithiapentalene-like structure.When diphenylketene was used as acylating reagent, the primary product (14), obtained at room temperature, rearranged on heating in a polar solvent into a δ2-thiazolin-4-one (15).The structure of 15 has been confirmed by X-ray analysis, and shown to be a zwitterion.Rearranged products (i.e., 16 and 20-22) were also obtained when 3 was reacted with dimethyl acetylenedicarboxylate or methanesulfonyl chloride, whereas tosyl chloride gave normal tosylated derivatives (17-19).The latter have also a nearly linear N-S...O arrangement, but the reaction between S and O is weak.
