Exploring the "fold-in" strategy toward the construction of a highly-strained triazasumanene skeleton
Fengkun Chen1, Takayuki Tanaka1, Atsuhiro Osuka1
1Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo-ku, Kyoto 606-8502, Japan. taka@kuchem.kyoto-u.ac.jp osuka@kuchem.kyoto-u.ac.jp.
Abstract:
The synthesis of tribenzotriazasumanene was attempted on the basis of the "fold-in" synthesis of cyclic pyrrole trimer 5 and its analogues under oxidative and reductive conditions. While unexpectedly triply-fused product 6 was obtained in the oxidation of 5 with FeCl3 and AgOTf, the reductive coupling of hexabromo-tri-N-methylpyrrole trimer 9 furnished partially fused product 10. These results indicate the potential of the "fold-in" strategy that gave complementary outcomes depending on the reaction conditions.
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