2024
DOI: 10.1002/ange.202411165
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Large Molecular Rotation in Crystal Changes the Course of a Topochemical Diels–Alder Reaction from a Predicted Polymerization to an Unexpected Intramolecular Cyclization

Anu Lal,
Mithun C. Madhusudhanan,
Kana M. Sureshan

Abstract: A designed anthracene‐based monomer for topochemical Diels‐Alder cycloaddition polymerization crystallized with head‐to‐tail arrangement of molecules, as revealed by single‐crystal X‐ray diffraction (SCXRD) analysis. The diene and dienophile units of adjacent monomer molecules are aligned at an average distance of 4.6 Å, suggesting a favorable crystalline arrangement for their intermolecular Diels‐Alder cycloaddition reaction to form a linear polymer . Surprisingly, heating the monomer crystals at a temperatur… Show more

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