Breaking paracyclophane: the unexpected formation of non-symmetric disubstituted nitro [2.2] metaparacyclophanes
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Date
2021
Open Access Location
Authors
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Publisher
Beilstein-Institut
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(c) The author/s
CC BY 4.0
CC BY 4.0
Abstract
Substituted [2.2]metaparacyclophanes are amongst the least studied of the simple cyclophanes. This is undoubtedly the result of the lengthy syntheses of these compounds. We report the simple synthesis of a rare example of a non-symmetric [2.2]metaparacyclophane. Treatment of [2.2]paracyclophane under standard nitration conditions gives a mixture of 4-nitro[2.2] paracyclophane, 4-hydroxy-5-nitro [2.2] metaparacyclophane and a cyclohexadienone cyclophane.
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Keywords
cyclophane, metaparacyclophane, nitration, paracyclophane, rearrangement
Citation
Patel S, Dais TN, Plieger PG, Rowlands GJ. (2021). Breaking paracyclophane: the unexpected formation of non-symmetric disubstituted nitro[2.2]metaparacyclophanes.. Beilstein J Org Chem. 17. (pp. 1518-1526).