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One‐Pot Synthesis to Quinone‐Based Diaza[3.3]cyclophanes
Author(s) -
Stahlhofen Jana Marie,
Schollmeyer Dieter,
Waldvogel Siegfried R.
Publication year - 2017
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201701124
Subject(s) - chemistry , quinone , cyclophane , alkylation , redox , anhydrous , combinatorial chemistry , benzoquinone , stereochemistry , organic chemistry , crystal structure , catalysis
A simple one‐pot synthesis to [3.3]cyclophanes that involves quinone moieties was found. The protocol tolerates a variety of amines that include aliphatic and aromatic structures with different functional groups, such as hydroxy groups, amides, and terminal double and triple bonds. The straightforward synthesis can be performed by a twofold N ‐alkylation reaction with 2,5‐bis(bromomethyl)‐3,6‐dimethyl‐1,4‐benzoquinone ( 1 ). Neither anhydrous nor inert conditions are required. Various amines can be employed without any activating groups, several functionalities at end groups are tolerated, and the cyclophanes generated can be easily modified or embedded into larger molecular architectures. The redox‐active nature of these cyclophanes allows their use in electron‐transfer processes.