1700-10-3Relevant articles and documents
Enantiodifferentiation in the Photoisomerization of (Z,Z)-1,3-Cyclooctadiene in the Cavity of γ-Cyclodextrin-Curcubit[6]uril-Wheeled [4]Rotaxanes with an Encapsulated Photosensitizer
Yan, Zhiqiang,Huang, Qinfei,Liang, Wenting,Yu, Xingke,Zhou, Dayang,Wu, Wanhua,Chruma, Jason J.,Yang, Cheng
, p. 898 - 901 (2017)
A biphenyl photosensitizer axle was implanted into the cavities of native and capped γ-cyclodextrins through rotaxanation using a cucubit[6]uril-templated azide-alkyne 1,3-dipolar cycloaddition, resulting in the construction of highly defined chiral binding/sensitizing sites. The orientation and interaction of the axle and capping moieties at the ground and excited states were interrogated by NMR, UV-vis, circular dichroism, and fluorescence spectroscopic studies. In situ photoisomerization of (Z,Z)-1,3-cyclooctadiene sensitized in the cavity of these [4]rotaxanes afforded (Z,E)-1,3-cyclooctadiene in up to 15.3% ee, which represents the highest level of enantiodifferentiation obtained to date for this supramolecular photochirogenesis.
Resolution, Circular Dichroism Spectrum, Molecular Structure, and Absolute Configuration of cis,trans-1,3-Cyclooctadiene
Isaksson, Roland,Roschester, Jan,Sandstroem, Jan,Wistrand, Lars-Goeran
, p. 4074 - 4075 (1985)
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Investigation of Rearrangement Reactions of Cyclic Allyl and Pentadienyl Anions
Sustmann, Reiner,Dern, Heinz-Juergen
, p. 2958 - 2971 (2007/10/02)
Bicyclohexenyl anion (1) and bicycloheptenyl anion (2) rearrange in THF to monocyclic pentadienyl anions, whereas bicyclooctenyl anion 3 is stable under the reaction conditions. 3 in contrary is formed by the known electrocyclic ring closure of cyclooctadienyl anion 7.Rearrangements of cyclopentenyl anion and pentadienyl anion are not detected.Cyclic allyl anions are alkylated by ethene, formed by cleavage of THF with base or independently added. 6,6-Dimethylcyclohexadienyl anion undergoes slow fragmentation to toluene at room temperature.