TY - JOUR
T1 - Cucurbiturils as Reaction Containers for Photocycloaddition of Olefins
AU - Pattabiraman, Mahesh
AU - Sivaguru, Jayaraman
AU - Ramamurthy, V.
N1 - Publisher Copyright:
© 2018 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
PY - 2018/4
Y1 - 2018/4
N2 - The [2+2] photocycloaddition (PCA [2+2]) of alkenes is one of the most synthetically useful photoreactions. It is a convenient one-step reaction that is useful for generating substituted cyclobutanes, polymers, and biologically relevant molecules. However, the reaction efficiency is limited by its bimolecular nature requiring encounter between two reactants within the narrow window of excited state lifetime of the photoactive alkene, and competition from the unimolecular photoisomerization. Our groups have utilized macrocyclic cavitands, especially cucurbiturils(CB), to confine two alkene molecules within their cavities and steer them towards a single dimer regio- and stereoselectively. Although, primarily the review focuses on photocycloaddition within CBs, such reactions in closely related cavitands such as cyclodextrins (CD) and calixarenes (CA) are also briefly mentioned to provide a comparison with CBs. Studies on photocycloaddition of olefins within CB by other research groups are also briefly highlighted. A mechanistic model, with ability to predict the nature of the dimer product formed within the above reaction containers is included.
AB - The [2+2] photocycloaddition (PCA [2+2]) of alkenes is one of the most synthetically useful photoreactions. It is a convenient one-step reaction that is useful for generating substituted cyclobutanes, polymers, and biologically relevant molecules. However, the reaction efficiency is limited by its bimolecular nature requiring encounter between two reactants within the narrow window of excited state lifetime of the photoactive alkene, and competition from the unimolecular photoisomerization. Our groups have utilized macrocyclic cavitands, especially cucurbiturils(CB), to confine two alkene molecules within their cavities and steer them towards a single dimer regio- and stereoselectively. Although, primarily the review focuses on photocycloaddition within CBs, such reactions in closely related cavitands such as cyclodextrins (CD) and calixarenes (CA) are also briefly mentioned to provide a comparison with CBs. Studies on photocycloaddition of olefins within CB by other research groups are also briefly highlighted. A mechanistic model, with ability to predict the nature of the dimer product formed within the above reaction containers is included.
KW - Cavitands
KW - Cucurbituril
KW - Host-guest complex
KW - Photocycloaddition
KW - Supramolecular chemistry
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U2 - 10.1002/ijch.201700100
DO - 10.1002/ijch.201700100
M3 - Review article
AN - SCOPUS:85038105671
SN - 0021-2148
VL - 58
SP - 264
EP - 275
JO - Israel Journal of Chemistry
JF - Israel Journal of Chemistry
IS - 3
ER -