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|Title:||Synthesis and conformational study of 1,1′-ethano-9-9′-bifluorenyl. Anti and gauche conformers of a 9,9′-bifluorenyl derivative and chair and twist conformers of a dibenzo-1,5-cyclooctadiene derivative|
|Authors:||Lai, Y.-H. |
|Source:||Lai, Y.-H.,Lee, S.-M.,Lee, S.-Y.,Yi, M. (1993-03-19). Synthesis and conformational study of 1,1′-ethano-9-9′-bifluorenyl. Anti and gauche conformers of a 9,9′-bifluorenyl derivative and chair and twist conformers of a dibenzo-1,5-cyclooctadiene derivative. Tetrahedron 49 (12) : 2437-2446. ScholarBank@NUS Repository.|
|Abstract:||A Hofmann-type elimination of the sulphonium salt (18) under basic conditions led to the formation of a novel o-xylylene derivative (11) which dimerized regioselectively to give the bifluorenyl/dibenzo-1,5-cyclooctadiene derivative (3). The reaction is shown to be kinetically controlled and non-concerted. The two rigid conformers (3a) and (3b) were characterised by their 1H NMR spectra and they represent respectively the first observed examples of an anti bifluorenyl derivative and a twist dibenzo-1,5-cyclooctadiene derivative. A semiempirical molecular orbital PM3 calculation supported the observed results. Dynamic 1H NMR studies indicated an interconversion process (3a) ⇄ (3b) at higher temperatures involving a conformational barrier estimated at 65.2 kJ mol-1. © 1993.|
|Appears in Collections:||Staff Publications|
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