T. L. Gilchrist
2005
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Abstract
Recent methods for the preparation of compounds bearing a carbonnitrogen double bond and two heteroatom substituents on carbon are described. The chapter is restricted to compounds with at least one halogen substituent (usually chlorine of bromine) and to those with at least one chalcogen (oxygen, sulfur, or selenium). The most important classes of such compounds are carbonimidic dichlorides (also known as isocyanide dichlorides), isoureas, isothioureas, and isoselenoureas. Carbonimidic dichlorides are available by a variety of methods, including addition of chlorine to isocyanides and chlorination of isothiocyanates. Several of the other compounds in this chapter can be obtained from carbonimidic dichlorides by nucleophilic displacement of one or both chlorine atoms. Isothioureas and isoselenoureas are most commonly obtained by alkylation of thioureas and selenoureas.