Abstract
Nitroacetylene (1 ) was prepared by the
reaction of NO2 PF6 with trimethylsilylacetylene.
It is stable at room temperature in dilute solution for about a
week. The 1 H and 13 C
NMR spectra of nitroacetylene reveal strong 1 H-14 N
and 13 C-14 N
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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