Cyclopropane-1,1-dicarbonitrile alkene

Cyclopropane-1,1-dicarbonitriles 1 were produced in fair to good yield by the reaction of di-bromomalonodinitrile with alkenes in the presence of a stoichiometric quantity of a copper(I) salt. ... 

Cyclopropane-1,1-dicarbonitriles were also obtained from bromomalonodinitrile and alkenes in the presence of a base (see Houben-Weyl, Vol.4/3, p369 and Section 1.1.3.7.1.). In a modification of this procedure, cyclopropanation of l,l-dichloro-4-methylpenta-l,3-diene to give 2 was performed in the presence of a copper(I) salt. ... 

Table 2. Cyclopropane-1,1-dicarbonitriles by Thermolysis of Diazomalononitrile in Different Alkenes and Arenes as Solvent...

The copper salt mediated synthesis of 1-alkoxycarbonylcyclopropane-l-carbonitriles from cy-anoacetates and alkenes or l,l-dichloro-4-methylpenta-1,3-diene is described in Section 1.2.1.2.4.2.9. An analogous synthesis of cyclopropane-1,1-dicarbonitriles has been claimed. Instead of l,l-dichloro-4-methylpenta-l,3-diene, 3,4-dibromo-l,l-dichloro-4-methylpent-l-ene can be utilized to form 1 (no yield given). ... 

By analogy to a synthesis of 1,1-dialkoxycarbonylcyclopropanes and 1-ethoxycarbonylcyclo-propane-l-carbonitriles from alkenes and malonic esters or cyanoacetic esters, respectively (see Section 1.2.1.2.4.2.9.), cyclopropane-1,1-dicarbonitriles were obtained from 1,3-dienes and malonodinitrile in the presence of iodine and solid potassium carbonate under phase-transfer conditions. ... 

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