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DOI: 10.1055/s-2002-34387
Nitroacetylene: HC≡CNO2
Publication History
Publication Date:
26 September 2002 (online)
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Abstract
Nitroacetylene (1) was prepared by the reaction of NO2PF6 with trimethylsilylacetylene. It is stable at room temperature in dilute solution for about a week. The 1H and 13C NMR spectra of nitroacetylene reveal strong 1H-14N and 13C-14N spin couplings. Nitroacetylene reacts rapidly with nucleophiles. It gives a 1,4-Diels-Alder adduct with cyclopentadiene. However, its reactions with furan and vinyl ethers produce nitrovinylisoxazoles by a mechanism thought to involve the 1,4-addition of nitroacetylene to the vinyl ether to give a highly strained unsaturated nitrone, followed by fragmentation of the nitrone to vinyl nitrile oxide, then additions of this 1,3-dipolarophile.
Key words
nitroacetylene - alkynes - Diels-Alder reactions - vinyl nitrile oxide - isoxazoles - heterocylcles
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We have recently had some success using nitronium triflate, an easily purified material.
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22From the 14N-decoupled, 1H-coupled spectrum.