Tetrahedron Letters p. 5887 - 5890 (1995)
Update date:2022-08-03
Topics:
Fehr
Fehr, Olaf C.
Grapenthin
Grapenthin, Olaf
Kilian
Kilian, Joerg
Kirmse
Kirmse, Wolfgang
Steenken
Steenken, Steen
Photolysis of 3,3-disubstituted 3H-indazoles in protic media (ROH) gives rise to benzyl ethers, in addition to hydrocarbons (derivatives of benzocyclopropene, styrene, and fluorene) which are also found in aprotic solvents. In the presence of ROD, the benzyl ethers are formed with incorporation of deuterium into the ortho position, pointing to protonation of 2-methylene-3,5-cyclohexadienylidenes. Laser flash photolysis of 3H-indazoles generates diazo compounds and benzyl cations as transient intermediates.
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