381173-20-2Relevant academic research and scientific papers
Diatropicity of 3,4,7,8,9,10,13,14-octadehydro[14]annulenes: A combined experimental and theoretical investigation
Boydston, Andrew J.,Haley, Michael M.,Williams, Richard Vaughan,Armantrout, John R.
, p. 8812 - 8819 (2002)
The synthesis and study of a series of octadehydro[14]annulenes is described. The aromaticity of these annulenes was investigated through examination of experimental data from arene-fused systems as well as calculated nucleus-independent chemical shifts (NICS) and bond lengths. Benzene ring fusion to the parent system results in a stepwise loss in aromaticity as the number of fused rings is increased from one to two to three. This decrease in annulenic ring current is manifested in the alkene proton chemical shifts (0-2 benzenes) as well as the NICS (0-3 benzenes). Comparison of isomeric thiophene-fused annulenes shows further evidence of ring current competition as these allow for observation of intermittent degrees of delocalization throughout the annulenic core. A consistent relationship between the magnitude of the NICS values and the degree of benzannelation is also observed.
Diatropicity of dehydrobenzo[14]annulenes: Comparative analysis of the bond-fixing ability of benzene on the parent 3,4,7,8,9,10,13,14-octadehydro[14]annulene
Boydston,Haley, Michael M.
, p. 3599 - 3601 (2007/10/03)
(matrix presented) We report the synthesis of 3,4,7,8,9,10,13,14-octadehydro[14]annulene (1) and detail a comparative aromaticity study with its benzannelated derivatives (e.g., 2 and 3).
