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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

submitted on 16.06.2020, 22:25 and posted on 18.06.2020, 08:09 by 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.


Department of Science and Technology (DST), grant no. ECR/2016/000441

Department of Science and Technology (DST), grant no. SB/S2/RJN-047/2015


Email Address of Submitting Author


Institute of Nano Science and Technology



ORCID For Submitting Author


Declaration of Conflict of Interest

The authors declare no competing financial interest.