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AD_TCNEO_GJ_ChemRxiv.pdf (4.96 MB)
New Access to the Synthesis of 1,1,4,4-Tetracyanobuta-1,3-Diene-Based Push–pull Chromophores Using Tetracyanoethylene Oxide via [3+2] Cycloaddition-Ring Opening Reactions
Preprints are manuscripts made publicly available before they have been submitted for formal peer review and publication. They might contain new research findings or data. Preprints can be a draft or final version of an author's research but must not have been accepted for publication at the time of submission.
submitted on 16.06.2020 and posted on 18.06.2020by Arif Hassan Dar, Vijayendran Gowri, Neethu K M, Govindasamy Jayamurugan
Herein we report a new way to access the synthesis of established invaluable push–pull chromophores based on 1,1,4,4-tetracyanobuta-1,3-dienes (TCBDs) using tetracyanoethylene oxide (TCNEO) upon reaction with alkynes substituted with an electron-donating group (EDG) via [3+2] cycloaddition (CA) followed by ring-opening (RO) reactions. Further, we uncovered that the facile [3+2] CA–RO reaction under simpler reaction condition is possible due to the presence of EDG group, otherwise, even the formation of [3+2] cycloadduct without EDG requires harsher condition and does not lead to TCBD as reported earlier in 1965 by Linn and Benson.