A cyclopenta[hi]acephenanthrylene bearing two benzoannelated [3.3.3]propellane units: extension of triptindane chemistry
作者： Hans-Georg Stammler , Dietmar Kuck , Thorsten Hackfort , Beate Neumann
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摘要: 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), sterically crowded stilbene hydrocarbon bearing two E-oriented triptindane moieties, in good yield. Photoisomerization 5 generated the corresponding cis-stilbene 8 photostationary E:Z mixture (55:45), which adopts similarly C2-symmetrical conformation that is apparently static on NMR timescale. Photocyclodehydrogenation via benzene solution afforded title 6, 1,2,9,10-tetrahydrocyclopenta[hi]acephenanthrylene merged with units, 85% X-ray structure analysis 6 revealed an essentially planar phenanthrene unit but significant steric repulsion between pairs opposite methylene groups cores, giving rise to conformation. Reaction 2 under modified conditions (DME instead THF as solvent) saturated dimer, 9,9′-b...
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Dietmar Kuck, From Fragmentation to Construction--from Void to Massive: Fascination with Organic Mass Spectrometry and the Synthesis of Novel Three-Dimensional Polycyclic Aromatic Hydrocarbons. Chemical Record. ,vol. 15, pp. 1075- 1109 ,(2015) , 10.1002/TCR.201500023
J. Drouin, F. Leyendecker, J.M. Conia, Thermolyse et photolyse de cetones non saturees—XXVIII : Double thermocyclisation des bis(butene-3' yl)-3,3-et bis(butyne-3' yl)-3,3-cyclopentanones: [3.3.3]propellanones fonctionnalisees en 2,8,9 Tetrahedron. ,vol. 36, pp. 1203- 1208 ,(1980) , 10.1016/0040-4020(80)87019-0
Hugh W. Thompson, Synthesis of a tricyclo[3.3.3.01,5]undecane system Tetrahedron Letters. ,vol. 7, pp. 6489- 6494 ,(1966) , 10.1016/S0040-4039(00)76131-4
Alois Fuerstner, Achim Hupperts, Carbonyl Coupling Reactions Catalytic in Titanium and the Use of Commercial Titanium Powder for Organic-Synthesis Journal of the American Chemical Society. ,vol. 117, pp. 4468- 4475 ,(1995) , 10.1021/JA00121A004
Jürgen Leimner, Peter Weyerstahl, Stereochemie und Nebenprodukte der reduktiven Kupplung von Alkylarylketonen zu 1,2‐Dialkyl‐1,2‐diarylethylenen Chemische Berichte. ,vol. 115, pp. 3697- 3705 ,(1982) , 10.1002/CBER.19821151203
P.W. Chum, Stanley E. Wilson, Reduction of alkynes and monosubstituted alkenes with lithium aluminum hydride and titanium tetrachloride Tetrahedron Letters. ,vol. 17, pp. 15- 16 ,(1976) , 10.1016/S0040-4039(00)71310-4
Dietmar Kuck, Andreas Schuster, Bernd Paisdor, Detlef Gestmann, Benzoannelated centropolyquinanes. Part 21. Centrohexaindane: three complementary syntheses of the highest member of the centropolyindane family Journal of The Chemical Society-perkin Transactions 1. ,vol. 6, pp. 721- 732 ,(1995) , 10.1039/P19950000721
Howard E. Simmons, John E. Maggio, Synthesis of the first topologically non-planar molecule Tetrahedron Letters. ,vol. 22, pp. 287- 290 ,(1981) , 10.1016/0040-4039(81)80077-9
Thorsten Hackfort, Dietmar Kuck, Phenanthro[1.10]-Annelated [3.3.3]Propellanes by Cyclodehydrogenation Reactions of Mono-, Di-, and Tribenzylidenetriptindanes European Journal of Organic Chemistry. ,vol. 1999, pp. 2867- 2878 ,(1999) , 10.1002/(SICI)1099-0690(199911)1999:11<2867::AID-EJOC2867>3.0.CO;2-B
Dietmar Kuck, Mass spectrometry of alkylbenzenes and related compounds. Part I. Gas‐phase ion chemistry of alkylbenzene radical cations Mass Spectrometry Reviews. ,vol. 9, pp. 187- 233 ,(1990) , 10.1002/MAS.1280090203