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Updated: Jul 1, 2025
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Solid-phase Synthesis of [4.4] Spirocyclic Oximes
Published on: February 6, 2019
From Serendipity to Precision: Decoding the Enigma of Rearrangement in Scholl-Type Reactions for Programmable
Nagaraju Ponugoti1, Sudhakar Maddala1, Parthasarathy Venkatakrishnan1
1Department of Chemistry, Indian Institute of Technology Madras, Chennai 600 036, Tamil Nadu, India.
Abstract:
Rearrangements in the Scholl reaction have traditionally been serendipitous, lacking a systematic approach for synthesizing rearranged and cyclized products. This paper introduces a strategic pathway to achieve rearranged-cyclized thienotetrahelicene derivatives over direct-cyclized chrysenothiophene derivatives by finely modifying the reaction conditions and tuning the electronic properties in Scholl-type reaction precursors, tetraarylthiophenes. Through careful design principles, we demonstrate the programmable synthesis of these distinct products.
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