Breaking paracyclophane: the unexpected formation of non-symmetric disubstituted nitro[2.2]metaparacyclophanes

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 unde...

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Bibliographic Details
Published in:	Beilstein journal of organic chemistry Vol. 17; no. 1; pp. 1518 - 1526
Main Authors:	Patel, Suraj, Dais, Tyson N, Plieger, Paul G, Rowlands, Gareth J
Format:	Journal Article
Language:	English
Published:	Germany Beilstein-Institut zur Föerderung der Chemischen Wissenschaften 2021 Beilstein-Institut
Subjects:	Carbon Chemistry Crystal structure Cyclophane Full Research Paper metaparacyclophane Nitration paracyclophane Polymerization rearrangement cyclophane paracyclophane metaparacyclophane rearrangement nitration
Online Access:	Get full text
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Summary:	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.
Bibliography:	ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 23
ISSN:	1860-5397 2195-951X 1860-5397
DOI:	10.3762/bjoc.17.109