AI Article Synopsis
- trans-3-(4'-Pyridyl)acrylic acid (4-PA) does not engage in photodimerization reactions unless it forms salts with different acids, which activates its photoreactivity.
- The anions from these salts are crucial in organizing the molecular packing of 4-PAH(+) in solid form, resulting in specific alignments.
- Depending on the anion present, either head-to-tail (HT) or head-to-head (HH) configurations are formed leading to distinct cyclobutane derivatives, which can later undergo isomerization in acidic conditions.
Article 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(3)CO(2)(-), Cl(-), ClO(4)(-), and BF(4)(-) direct the parallel alignments of 4-PAH(+) in head-to-tail (HT) fashion and lead to the formation of HT-photodimer. On the other hand, bivalent anion SO(4)(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 anion-controlled 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.
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| http://dx.doi.org/10.1021/jo201268p | DOI Listing |
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