Zur Chemie der α‐Thiocarbamoylcarbodiimide

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Abstract
Chemistry of α‐ThiocarbamoylcarbodiimidesThe dipolar species 2a can be detected in equilibrium with the α‐thiocarbamoylcarbodiimide 1a by protonation and reduction to give 3 and 4, respectively. On heating, 1a rearranges to afford the photochromic dipole 7a. In addition to the formation of the derivatives 10 – 13, the molecular structure of 7a was confirmed by X‐ray structure analysis. In a subsequent rearrangement, 7a isomerizes to give 9a. The α‐carbamoylcarbodiimide 21 can be synthesized from the thiourea 20; the course of thiolysis to furnish the urea 24 indicates an equilibrium contribution of the dipolar species 22. The equilibrium compounds 1a, c ⇋ 2a, c undergo 2 + 2 cycloadditions with diphenylketene (25) to yield the four‐membered heterocycles 26a and b. The α‐carbamoylcarbodiimide 21 reacts with 25 to afford the ß‐lactam 30 and the 1:2 adduct 31.

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