Preparation and Molecular Structures of 9,10-Dihydrophenanthrenes:  Substituent Effects on the Long Bond Length

Preparation and Molecular Structures of 9,10-Dihydrophenanthrenes:  Substituent Effects on the Long Bond Length

9,10-Dihydrophenanthrene derivatives 1−3 with electron-donating and/or -accepting groups at their 9,10-positions were prepared, and their precise molecular structures were determined by X-ray analyses at 203 K. The long C9−C10 bond [1.646(4) Å] in the hexaarylethane-type compound 1 with four electro...

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Veröffentlicht in:Journal of organic chemistry 2000-08, Vol.65 (16), p.4944-4948
Hauptverfasser: Suzuki, Takanori, Ono, Kazunori, Nishida, Jun-ichi, Takahashi, Hyou, Tsuji, Takashi
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container_end_page 4948
container_issue 16
container_start_page 4944
container_title Journal of organic chemistry
container_volume 65
creator Suzuki, Takanori
Ono, Kazunori
Nishida, Jun-ichi
Takahashi, Hyou
Tsuji, Takashi
description 9,10-Dihydrophenanthrene derivatives 1−3 with electron-donating and/or -accepting groups at their 9,10-positions were prepared, and their precise molecular structures were determined by X-ray analyses at 203 K. The long C9−C10 bond [1.646(4) Å] in the hexaarylethane-type compound 1 with four electron-donating groups is mainly caused by steric interaction. Push−pull type substitution does not induce the elongation of the central bond in the present system; the corresponding distance in 9,9-bis(4-dimethylaminophenyl)-10,10-dicyano derivative 2 [1.599(4) Å] is intermediate between those of 1 and the tetracyano compound 3 [1.587(2) Å].
doi_str_mv 10.1021/jo0003697
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title Preparation and Molecular Structures of 9,10-Dihydrophenanthrenes:  Substituent Effects on the Long Bond Length
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