Stereo- and regioselective photocycloaddition of extended alkenes using γ-cyclodextrin
- 12 September 2018
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Organic & Biomolecular Chemistry
- Vol. 16 (38) , 6870-6875
Abstract
Photoexcitation of dibenzalacetones (1a–d) in homogeneous media and solid state yields a mixture of products with poor conversions. Irradiation of the reactants complexed to γ-cyclodextrin predominantly affords a single dimer (syn adduct 6) despite the possibility for several monomeric and dimeric products. High selectivity in the cavitand-mediated reaction along with the structural characterization of the inclusion complex provides insight into the supramolecular interactions that drive the self-assembly of the host–guest system.Keywords
Funding Information
- American Chemical Society Petroleum Research Fund (54862-UR4)
- National Institute of General Medical Sciences (1U54GM115458-01)
This publication has 29 references indexed in Scilit:
- Topochemical control of the photodimerization of aromatic compounds by γ-cyclodextrin thioethers in aqueous solutionBeilstein Journal of Organic Chemistry, 2013
- Cyclodextrin-based inclusion complexation bridging supramolecular chemistry and macromolecular self-assemblyChemical Society Reviews, 2011
- Topochemical Limits for Solid-State Photoreactivity by Fine Tuning of the π−π InteractionsJournal of the American Chemical Society, 2009
- Cyclobutane-Containing Alkaloids: Origin, Synthesis, and Biological ActivitiesThe Open Medicinal Chemistry Journal, 2008
- Photochemical Reactions as Key Steps in Organic SynthesisChemical Reviews, 2008
- Crystal engineering principles applied to solution photochemistry: controlling the photodimerization of stilbazolium salts within γ-cyclodextrin and cucurbit[8]uril in water2007
- Dinuclear Metal–Organic Material for Binary Optical RecordingAdvanced Functional Materials, 2003
- Enantiomerically Pure Cyclobutane Derivatives and Their Use in Organic SynthesisChemical Reviews, 2003
- Stereoselective Photodimerization of (E)-Stilbenes in Crystalline γ-Cyclodextrin Inclusion ComplexesThe Journal of Organic Chemistry, 1999
- Photodimerization of coumarins in solid cyclodextrin inclusion complexesThe Journal of Organic Chemistry, 1992