10432-75-4

Upstream product

• 109-77-3 malononitrile 
• 265108-11-0 2-(2-ethyl-butylidene)-malononitrile 
• 96-22-0 pentan-3-one 
• 1885-23-0 dibromomalononitrile 
• 1885-22-9 bromomalononitrile 
• 10394-95-3 (1-ethyl-propylidene)-malononitrile 

Relevant academic research and scientific papers

Engineering Crystals Using sp3-C Centred Tetrel Bonding Interactions

1,1,2,2-Tetracyanocyclopropane derivatives 1 and 2 were designed and synthesized to probe the utility of sp3-C centred tetrel bonding interactions in crystal engineering. The crystal packing of 1 and 2 and their 1,4-dioxane cocrystals is dominated by sp3-C(CN)2???O interactions, has significant C???O van der Waals overlap (≤0.266 ?) and DFT calculations indicate interaction energies of up to ?11.0 kcal mol?1. A cocrystal of 2 with 1,4-thioxane reveals that the cyclopropane synthon prefers interacting with O over S. Computational analyses revealed that the electropositive C2(CN)4 pocket in 1 and 2 can be seen as a strongly directional ‘tetrel-bond donor’, similar to halogen bond or hydrogen bond donors. This disclosure is expected to have implications for the utility of such ‘tetrel bond donors’ in molecular disciplines such as crystal engineering, supramolecular chemistry, molecular recognition and medicinal chemistry.

A new type of cascade reaction: direct conversion of carbonyl compounds and malononitrile into substituted tetracyanocyclopropanes

A new type of chemical cascade reaction was found: the direct formation of cyclopropanes from carbonyl compounds and C-H acid. The action of free halogen or active halogen containing compounds on a mixture of 1 equiv of carbonyl compound and 2 equiv of malononitrile in a basic alcohol solution results in the formation of substituted 1,1,2,2-tetracyanocyclopropanes in 15-80% yield. The latter are well-known precursors for the different bicyclic heterosystems, among them compounds containing a cyclopropane ring and possessing different types of pharmacological activity. Thus, the new, simple and efficient 'one-pot' way to substituted tetracyanocyclopropanes in 50-80% yield was found directly from such simple and reasonable starting compounds as aldehydes, or some cyclic ketones, or substituted cyclohexanones and malononitrile.

One-pot cascade assembling of 3-substituted tetracyanocyclopropanes from alkylidenemalononitriles and malononitrile by the only bromine direct action

The new cascade reaction was found: the formation of cyclopropanes from alkylidenemalononitriles and malononitrile by the only bromine direct action; the action of aqueous bromine on the equal amounts of alkylidenemalononitriles and malononitrile in EtOH-

Cyclopropanation of Electron-deficient Alkenes and Wideqvist-type Synthesis of Cyclopropanes mediated by Indium Metal

Cyclopropanation of electron-deficient alkenes and Wideqvist-type transformation of carbonyl compounds to cyclopropanes have been achieved by the action of active methylene dibromides and metallic indium.