Alkyl Shifts in 1,4‐Dipoles from Tosyl Iso(thio)cyanate and Imido(thio)carbonates or Isoureas

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Abstract
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). Similarly, 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.

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