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Tetraaminoethylene: Wikis

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Ethylenetetraamine.png

Tetraaminoethylene is a hypothetical organic compound with formula C2N4H8 or (H2N-)2C=C(-NH2)2. Like all geminal polyamines, this compound has never been synthesised and is believed to be extremelly unstable.[1]

However, there are many stable compounds that can be viewed as derivatives of this substance, with various organic functional groups substituted for some or all hydrogen atoms. These compounds, which have the general formula (R2N)2C=C(NR2)2, are collectively called tetraaminoethylenes.

Tetraaminoethylenes are important in organic chemistry as dimers of diaminocarbenes, a type of stable carbene with the general formula (R2N-)2C:.

Reactions

  • Tetraaminoethylenes react with acids to give formamidinium salts.
  • Tetraaminoethylenes react with oxygen to give urea derivatives (R2N)2C=O. A notorious example is the spontaneous reaction of octamethyltetraminoethylene ((H3C-)2N-)2C=C(-N(-CH3) 2)2 in air with emission of a green-blue light, which was used by downed US Navy pilots to signal for help in World War II.

References

  1. ^ Stephen A. Lawrence (2004), Amines: synthesis, properties and applications. Cambridge University Press. ISBN 0521782848, 371 pages.

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