Formimidoyl cyanide and isocyanide from azidoacetonitrile by photolysis
- 1 January 1975
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- No. 18,p. 1743-1747
- https://doi.org/10.1039/p19750001743
Abstract
Photoelimination of nitrogen from azidoacetonitrile (1) produced formimidoyl cyanide (2). At –196 °C further irradiation transformed the cyanide (2) into formimidoyl isocyanide (3); both (2) and (3), detected by i.r. absorption, can be intermediates in the formation of hydrogen cyanide and adenine (4) from a solution of (1) irradiated at 25–40 °C. Photodissociation of N-ethyl-(5a), N-isopropyl-(5b), and N-t-butyl-formimidoyl cyanide (5c) gave the corresponding N-alkyl isocyanide (7a–c)(3 %) at 25–40 °C and in detectable amounts at –196 °C. Azidoacetonitrile (1) at 125 °C dimerised to give 5H,10H-ditetrazolo[1,5-a:1′,5′-d]pyrazine(15).Keywords
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