Rearrangements of Tricyclo[5.3.1.0]undecatrienyl Anion; Chemical Evidence Supporting Cyclopropane Ring Circumambulation of Anionic Species

Rearrangements of Tricyclo[5.3.1.0]undecatrienyl Anion; Chemical Evidence Supporting Cyclopropane Ring Circumambulation of Anionic Species

The tricyclic anion 5, generated from the corresponding hydrocarbon 3 with n-BuLi, undergoes the circumambulatory rearrangement at −78 °C to afford the anion 6, which stereoselectively reacts with deuterium oxide at low temperature and undergoes further rearrangements to the stable cyclopentadienyl...

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Veröffentlicht in:Chemistry letters 1997-07, Vol.26 (7), p.595-596
Hauptverfasser: Oda, Mitsunori, Masaki, Yoshimi, Okazaki, Yoshimi, Kajioka, Takanori, Izawa, Mayumi, Miyatake, Ryuta, Kuroda, Shigeyasu, Scott, Lawrence T
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Sprache:eng
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Zusammenfassung:The tricyclic anion 5, generated from the corresponding hydrocarbon 3 with n-BuLi, undergoes the circumambulatory rearrangement at −78 °C to afford the anion 6, which stereoselectively reacts with deuterium oxide at low temperature and undergoes further rearrangements to the stable cyclopentadienyl anion derivative 9 at elevated temperature.
ISSN:0366-7022
1348-0715
DOI:10.1246/cl.1997.595