106115-14-4Relevant academic research and scientific papers
Alkyl Shifts in 1,4-Dipoles from Tosyl Iso(thio)cyanate and Imido(thio)carbonates or Isoureas
Schaumann, Ernst,Dietz, Joerg,Kausch, Erwin,Schmerse, Gerd C.
, p. 339 - 344 (2007/10/02)
O-->N alkyl shifts are observed in the dipoles 3, 13 from tosyl isocyanate (2a) and imido(thio)carbonates 1 (12) to give (thio)allophanates 5 (14).Similary, addition of tosyl isothiocyanate (2b) to isourea 24a leads to the product 28 of an O-->S methyl shift.A cross-over experiment involving 2a and imidothiocarbonates 12b,c gives the four products 14a-d proving the intermolecular nature of the rearrangement.However, on mixing 2a and isoureas 24a,b or 2b and imido(thio)carbonates 1 (12), the reaction stops at the stage of dipoles 8, 19, 25a,b.
