International Scholarly Research Notices / 2011 / Article / Tab 1

Research Article

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

Table 1

Direct transformation of benzaldehyde 1a, butanal 1k and cyclohexanone 1p with malononitrile 3 into substituted 1,1,2,2-tetracyanocyclopropanes 2 .

CarbonylSolventBromineCatalystYield of (%)

1aEtOHelemental2a, 12
1aEtOH/H2O0.2 M (H2O)2a, 90
1aEtOH/H2O0.2 M (H2O)NaOAc2a, 92
1kEtOH/H2O0.2 M (H2O)2k, 21
1kEtOH/H2O0.2 M (H2O)NaOAc2k, 86
1pEtOH/H2O0.2 M (H2O)2p, 43
1pEtOH/H2O0.2 M (H2O)NaOAc2p, 79

10 mmol of carbonyl compound 1, 20 mmol of malononitrile 3, 5 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.