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- W1593353656 abstract "Two strained bridgehead cage alcohols with a very short intramolecular OH...π distance, tetracyclo[5.3.0.0.2,5.0.4,8 dec-9-en-3-ol and its 3-methyl derivative, have been synthesized. The IR spectra have been studied and discussed in relation to the starting ketone tetracyclo[5.3.0.2,5.0.0.4,8] dec-9-en- 3-one. Considerable attractive OH-proton...π-electron interaction on the one hand and repulsive steric and oxygen-lone-pair... π forces on the other hand lead to a position of the hydroxyl bond, practically parallel to the double bond. Non-bonding proton..proton interaction in the 3-methyl compound causes increased C-H stretching frequencies of the alkyl groups involved. The IR-data of the ketone confirms the presence of non-bonding π-orbital interaction and shows the C=O vibration is subject to Fermi resonance." @default.
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- W1593353656 date "1988-01-01" @default.
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- W1593353656 title "Short intramolecular oh...π - electron distances in rigid polycyclic structures" @default.
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- W1593353656 doi "https://doi.org/10.1016/s0040-4020(01)85920-2" @default.
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