Synthesis and structural characterization of 5,6,15,16-tetradehydrobenzo[a]phenanthro[9, 10-e]cyclooctene,C24H12 |
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Authors: | Chun-Yip Leung Thomas C W Mak Henry N C Wong |
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Institution: | (1) Department of Chemistry, The Chinese University of Hong Kong, Shatin, New Territories, Hong Kong;(2) Present address: Department of Chemistry, The University of Hong Kong, Pokfulam Road, Hong Kong |
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Abstract: | A benzo-phenanthro-fused planar cyclooctatetraene derivative, namely, 5,6,15,16-tetradehydrobenzoa]phenanthro9, 10-e]cyclooctene (5) was synthesized in two steps from the known benzoa]phenanthro9, 10-e]cyclooctene (6). Compound5 crystallizes in space groupPbam witha=9.828(2),b=19.466(4),c=15.901(3) Å, and Z=8. X-Ray analysis (MoK radiation,R=0.060 for 1233 observed data) has shown that both independent molecules have the same planarC
2v
configuration with averaged bond lengths of 1.381(7) and 1.208(7) Å for the phenanthrene C6a–C14b bond and the acetylenic C C bond, respectively.1H and13C NMR spectral results of 5 and 5,6,15,16-tetrabromo-5,6,15,16-tetrahydrobenzoa]phenanthro9, 10-e]cyclooctene (7) are also presented. |
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Keywords: | 5 6 15 16-Tetradehydrobenzo[a]phenanthro[9 10-e]cyclooctene planar dehydro[8]annulenes angle-strained alkynes |
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