31366-37-7Relevant academic research and scientific papers
Dissolving Metal Reduction of Aceanthrylene and NMR Analysis of a Rigid, Boat-Shaped 9,10-Dihydroanthracene
Rabideau, Peter W.,Mooney, Jennifer L.,Smith, W. Kimmer,Sygula, Andrzej,Paschal, Jonathan W.
, p. 589 - 591 (2007/10/02)
Aceanthrylene is reduced by sodium/ammonia solution to its 2,6-dihydro derivative (4), which indicates a protonation site in the dianion in contrast to the MNDO-calculated position of highest electron density.It is concluded that monoanion stability must be the prevailing feature.Compound 4 is also reduced by sodium/ammonia to provide 1,9-ethano-9,10-dihydroanthracene, which allowed the first proton NMR study of a rigid, boat-shaped dihydroanthracene.Especially interesting are the long range, five-bond homoallylic couplings between the 9- and 10-positions, and the values measured are 4.7 Hz for 5J9,10 (dipseudoaxial) and 1.4 Hz for 5J9,10' (pseudoaxial/pseudoequatorial).The protonation and alkylation of (3-phenylindenyl)lithium is also considered so as to better understand the behavior of the intermediates derived from aceanthrylene.
Sigmatropic Indenyl Rearrangements Induced by Electronic Excitation
Padwa, Albert,Goldstein, Steven,Loza, Roman,Pulwer, Mitchell
, p. 1858 - 1868 (2007/10/02)
The photochemical rearrangement of several arylalkyl substituted indenes has been studied.The rearrangements were shown to be derived from the ?,?* singlet state since triplet sensitization led to no reaction or else resulted in a Paterno-Buchi
