From Carbonimidoyl Dihalides

The reaction of carbonimidoyl dichlorides with alkoxide or phenoxide ion is perhaps the most general synthetic procedure for 1-chloroformimidates XIII. While generally the alkoxides or phenoxides are used (80.20,35, Ktihle ( ) has shown that aqueous sodium hydroxide and alcohols work equally well. 

Similarly, reaction of thiolate ion with carbonimidoyl dichlorides affords the 1-chlorothioformimidates XIV 

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All in all a great variety of compounds can be synthesized from carbonimidoyl dihalides, and their use as agricultural chemicals has been indicated in the patent literature (17,27,29,48,65,88,94,99.144 ... 

Abstraction of the halo groups from carbonimidoyl dihalides (reversal of their syntheses) to yield isocyanides can be achieved by the use of triphenyl and tributylphosphine... 

Iminophosphoranes can also be used to synthesize symmetrical carbodiimides. In this case they are reacted with carbon dioxide, thereby mimicking the synthesis of carbodiimides from amines and carbon dioxide. Another useful synthesis of unsymmetrical carbodiimides, not requiring the use of carbonyl chloride, is the reaction of carbonimidoyl dihalides with amines. The synthesis and chemistry of carbonimidoyl halides was reviewed in 1968. ... 

Thus, reaction of carbonimidoyl dihalides with a wide variety of nitrogen-containing substrates can be achieved, and the products obtained range from linear chloroformamidines, guanidines, and carbodiimides to five- and six-membered heterocycles. 

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