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Synthesis of 1,1,4,4‐Tetracyanobuta‐1,3‐Dienes using Tetracyanoethylene Oxide via [3+2]‐Cycloaddition‐Ring Opening Reaction
Author(s) -
Dar Arif Hassan,
Gowri Vijayendran,
Neethu K. M.,
Jayamurugan Govindasamy
Publication year - 2020
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.202003179
Subject(s) - tetracyanoethylene , cycloaddition , deoxygenation , chemistry , ring (chemistry) , chromophore , oxide , photochemistry , medicinal chemistry , organic chemistry , catalysis
Unlike the [3+2] cycloadduct of electron‐donating group (EDG)‐free alkynes with tetracyanoethylene oxide (TCNEO), the EDG induced [3+2] cycloadduct underwent one‐pot ring‐opening and deoxygenation reactions to provide the established EDG‐substituted non‐planar 1,1,4,4‐tetracyanobuta‐1,3‐dienes (TCBDs) push‐pull chromophores. This is an alternate synthetic method that provides access to TCBDs other than the [2+2] cycloaddition–retroelectrocyclization reactions with tetracyanoethene.