A cyclopenta[hi]acephenanthrylene bearing two benzoannelated [3.3.3]propellane units: extension of triptindane chemistry

Hackfort T, Neumann B, Stammler H-G, Kuck D (2017)
CANADIAN JOURNAL OF CHEMISTRY 95(4): 390-398.

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Zeitschriftenaufsatz | Veröffentlicht | Englisch
Abstract / Bemerkung
The McMurry reaction of triptindan-9-one (2), a three-fold benzoannelated Cs-symmetrical [3.3.3]propellane ketone, gave trans-9,9'-bitriptindanylidene (5), a sterically crowded stilbene hydrocarbon bearing two E-oriented triptindane moieties, in good yield. Photoisomerization of 5 generated the corresponding cis-stilbene 8 in a photostationary E:Z mixture (55: 45), which adopts a similarly crowded C-2-symmetrical conformation that is apparently static on the NMR timescale. Photocyclodehydrogenation of 5 via 8 in benzene solution afforded the title hydrocarbon 6, a 1,2,9,10-tetrahydrocyclopenta[hi]acephenanthrylene merged with two triptindane units, in 85% yield. X-ray structure analysis of 6 revealed an essentially planar phenanthrene unit but significant steric repulsion between the pairs of opposite methylene groups of the [3.3.3] propellane cores, giving rise to a C2-symmetrical conformation. Reaction of 2 under modified McMurry conditions (DME instead of THF as a solvent) gave the saturated dimer, 9,9'-bitriptindanyl 7, as a mixture of diastereomers. Attempts to synthesize "columnene" (4), an elusive barrelene derivative fused with two triptindane caps, by three-fold McMurry reaction of triptindane-9,10,11-trione (3) failed.
Erscheinungsjahr
Zeitschriftentitel
CANADIAN JOURNAL OF CHEMISTRY
Band
95
Zeitschriftennummer
4
Seite
390-398
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eISSN
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Hackfort T, Neumann B, Stammler H-G, Kuck D. A cyclopenta[hi]acephenanthrylene bearing two benzoannelated [3.3.3]propellane units: extension of triptindane chemistry. CANADIAN JOURNAL OF CHEMISTRY. 2017;95(4):390-398.
Hackfort, T., Neumann, B., Stammler, H. - G., & Kuck, D. (2017). A cyclopenta[hi]acephenanthrylene bearing two benzoannelated [3.3.3]propellane units: extension of triptindane chemistry. CANADIAN JOURNAL OF CHEMISTRY, 95(4), 390-398. doi:10.1139/cjc-2016-0498
Hackfort, T., Neumann, B., Stammler, H. - G., and Kuck, D. (2017). A cyclopenta[hi]acephenanthrylene bearing two benzoannelated [3.3.3]propellane units: extension of triptindane chemistry. CANADIAN JOURNAL OF CHEMISTRY 95, 390-398.
Hackfort, T., et al., 2017. A cyclopenta[hi]acephenanthrylene bearing two benzoannelated [3.3.3]propellane units: extension of triptindane chemistry. CANADIAN JOURNAL OF CHEMISTRY, 95(4), p 390-398.
T. Hackfort, et al., “A cyclopenta[hi]acephenanthrylene bearing two benzoannelated [3.3.3]propellane units: extension of triptindane chemistry”, CANADIAN JOURNAL OF CHEMISTRY, vol. 95, 2017, pp. 390-398.
Hackfort, T., Neumann, B., Stammler, H.-G., Kuck, D.: A cyclopenta[hi]acephenanthrylene bearing two benzoannelated [3.3.3]propellane units: extension of triptindane chemistry. CANADIAN JOURNAL OF CHEMISTRY. 95, 390-398 (2017).
Hackfort, Thorsten, Neumann, Beate, Stammler, Hans-Georg, and Kuck, Dietmar. “A cyclopenta[hi]acephenanthrylene bearing two benzoannelated [3.3.3]propellane units: extension of triptindane chemistry”. CANADIAN JOURNAL OF CHEMISTRY 95.4 (2017): 390-398.