Addition and Cycloaddition Reactions of Tetracyanoethylene (TCNE) in Organic Chemistry

Pyrazole, pyrazolo[1,2-c]-1,3,4-thiadiazole and thiadiazepine derivatives from thiosemicarbazides

“…1 2,4-Tetracyanoethene 2 has an impressive variety of potential applications. [15][16][17] Tetracyanoethene is an established reagent for reacting with ene, diene, and various other rich electron systems in organic and metallo-organic substrates. In addition, 2 is a useful reagent for synthesis of cyanocarbon acids, spiro compounds and novel heterocycles.…”

“…In addition, 2 is a useful reagent for synthesis of cyanocarbon acids, spiro compounds and novel heterocycles. [15][16][17][18][19][20][21] Recently, it has been reported that 4-phenyl-and 4-benzylthiosemicarbazides 1a,b reacted with 2 in ethyl acetate with charge-transfer complex (CT) formation, ultimately giving a mixture of thiadiazepine and thiadiazole derivatives 3-5 ( Figure 1). 22 …”

Unexpected condensation reaction of two units of 1,2‐dihydrophosphinine 1‐oxides in the presence of tetracyanoethylene

“…Recently, we have aimed at the synthesis of new types of precursors, such as diaza derivatives [4,5] or the dimers of dihydrophosphinine oxides [5,6]. In this paper, we describe the reactions of dihydrophosphinine oxides with tetracyanoethylene, which is a versatile dienophile that sometimes gives quite unexpected results [7][8][9].…”

Pyridine-Functionalized MCM-41 as an Efficient and Recoverable Catalyst for the Synthesis of Pyran Annulated Heterocyclic Systems

“…TCNE has received an extensive amount of study and the chemistry of this compound has been reviewed several times. [8][9][10] The mesoporous molecular sieves such as MCM-41 which discovered by Mobil researchers in 1992, have large and uniform pore sizes, ultrahigh surface areas, large pore volume and rich silanol groups in the inner walls. The developments of mesoporous silicas such as MCM-41 have generated interest due to their potential applications such as catalysts, catalyst supports, separation media, and host materials for inclusion compounds.…”