Please use this identifier to cite or link to this item: https://doi.org/10.1021/jo201268p
Title: Role of anions in the synthesis of cyclobutane derivatives via [2 + 2] cycloaddition reaction in the solid state and their isomerization in solution
Authors: Kole, G.K.
Tan, G.K.
Vittal, J.J. 
Issue Date: 7-Oct-2011
Citation: Kole, G.K., Tan, G.K., Vittal, J.J. (2011-10-07). Role of anions in the synthesis of cyclobutane derivatives via [2 + 2] cycloaddition reaction in the solid state and their isomerization in solution. Journal of Organic Chemistry 76 (19) : 7860-7865. ScholarBank@NUS Repository. https://doi.org/10.1021/jo201268p
Abstract: Trans-3-(4′-Pyridyl)acrylic acid (4-PA) is inert to photodimerization reaction both in solution and solid state. It is made photoreactive by forming salts with various acids. The anions of these salts play a key role in directing the packing of 4-PAH+ in the solid state. The anions CF 3CO2 -, Cl-, ClO4 -, and BF4 - direct the parallel alignments of 4-PAH+ in head-totail (HT) fashion and lead to the formation of HT-photodimer. On the other hand, bivalent anion SO4 2- directs parallel alignment of 4-PAH+ in head-to-head (HH) fashion and lead to the formation of HH-photodimer. The details of the anioncontrolled stereoselective syntheses of these two cyclobutane derivatives are presented. Interestingly, both cyclobutane compounds undergo isomerization from rctt-form to rctc-form in solution catalyzed by acid. (Figure presented) © 2011 American Chemical Society.
Source Title: Journal of Organic Chemistry
URI: http://scholarbank.nus.edu.sg/handle/10635/94729
ISSN: 00223263
DOI: 10.1021/jo201268p
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