International Scholarly Research Notices / 2011 / Article / Tab 2

Research Article

New Way to Substitute Tetracyanocyclopropanes: One-Pot Cascade Assembling of Carbonyls and Malononitrile by the Only Bromine Direct Action

Table 2

Direct transformation of carbonyl compounds 1ar and malononitrile 3 into substituted 1,1,2,2-tetracyanocyclopropanes 2ar by the action of bromine in EtOH/water system.

OlefinR1R2ProductYield of (%)

1aHPh2a92
1bH4-MeC6H42b91
1cH4-MeOC6H42c93
1dH3-MeOC6H42d91
1eH2-MeOC6H42e92
1fH4-FC6H42f90
1gH4-ClC6H42g85
1hH3-ClC6H42h87
1iH3-BrC6H42i92
1jH4-NO2C6H42j88
1kHn-Pr2k86
1lMeMe2l55
1mMeEt2m52
1nEtEt2n48
1o– (CH2)42o69
1p– (CH2)52p75
1r– (CH2)62r67

10 mmol of carbonyl compound 1, 20 mmol of malononitrile 3, 3 mmol of NaOAc, 20 mL of EtOH, 50 mL of 0.2 M Br2 in water (10 mmol), temperature 40°C, time of reaction 1 hour.
Yield of isolated product.