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April 10, 2026Organic Letters0 citations

An Exclusive Synthesis of Macrocyclic Trimer over Polymers

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JZJunqing ZhangUniversity of Alaska FairbanksYZYunshen ZhouUniversity of Science and Technology of ChinaJMJiawei MaMinistry of Education

Key Points

  • This research aims to explore the conditions that favor the synthesis of a macrocyclic trimer over linear polymers.
  • Utilized 1,2,3,4-tetramethoxybenzene and paraformaldehyde in dynamic reaction conditions.
  • Monitored the reaction progression using NMR to track oligo- and macrocyclic transformations.
  • Applied DFT studies to analyze the thermodynamics of the cyclic trimer formation.
  • Achieved exclusive synthesis of the macrocyclic trimer, bypassing undesired polymer formation.
  • NMR data indicated a stepwise conversion of linear intermediates to the cyclic product.
  • DFT findings confirmed that the macrocyclic trimer is thermodynamically preferable among potential products.

Abstract

Despite the inherent competition between cyclization and linear polymerization, we report the exclusive synthesis of a macrocyclic trimer from 1,2,3,4-tetramethoxybenzene and paraformaldehyde. Dynamic Friedel-Crafts alkylation proceeds solely through linear oligomeric intermediates, which ultimately convert to the cyclic trimer without polymer formation. NMR monitoring tracks this stepwise conversion, and DFT studies identify the cyclic trimer as the thermodynamically favored product among accessible species. This system circumvents the cyclization-polymerization equilibrium, providing insight into the competition mechanism under macrocycle synthesis.

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Cite This Study

Zhang et al. (2026) studied this question.

synapsesocial.com/papers/69d8948f6c1944d70ce0576chttps://doi.org/10.1021/acs.orglett.6c01048
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