Helvetica Chimica Acta p. 835 - 848 (1986)
Update date:2022-08-17
Topics:
Krebs, Juerg
Guggisberg, Dominik
Staempfli, Urs
Neuenschwander, Markus
Triafulvene precursors exo-15 and endo-15 have been prepared by addition of dibromocarbene to benzobarrelene 12 followed by a lithium-halogen exchange, methylation, and elimination of HBr (12 -> 13 -> 14 -> 15), (Scheme 2).Gas-phase pyrolysis of exo/endo-mixtures of 15 above 400 deg gave minor amounts of naphthalene (16), traces of a hydrocarbon C4H4 identified by MS (presumably triafulvene 1) and predominantly (36percent) the isomerization product 17 (Scheme 3).In a second synthetic approach the well-known cycloheptatriene-norcaradiene equilibrium of type 26->/<-27 has been utilised to prepare various endo-trans-3-(X-methyl) tricyclo<3.2.2.02,4>nona-6,8-dienes 31 (Scheme 5).However, numerous elimination experiments 31 -> 9 failed so far.The structure of two rearrangement products 33 and 34 (Scheme 6) has been elucidated.
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