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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

preprint
submitted on 16.06.2020 and posted on 18.06.2020 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.

Funding

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

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

History

Email Address of Submitting Author

jayamurugan@inst.ac.in

Institution

Institute of Nano Science and Technology

Country

India

ORCID For Submitting Author

0000-0001-9870-5209

Declaration of Conflict of Interest

The authors declare no competing financial interest.

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