Tetrahedron Letters p. 61 - 64 (1984)
Update date:2022-07-29
Topics:
Huisgen, Rolf
Bronberger, Franz
The title reaction, carried out without solvent at -50 deg C raised to room temperature, produces the hydrazonic 1:2 adduct 6 and the 1:3 adducts 9a and 9b whereas in methanol at -10 deg C the intermediate cyclopentadienone-4-nitrophenylhydrazone (5) adds a solvent molecule; the azo coupling does not require the cyclopentadienide anion, as demonstrated by the behavior of spiro<2.4>heptadiene (12).
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