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An Efficient Route to Symmetrical and Unsymmetrical Disulfide, Thioether, and Hydrocarbon Cyclophanes
Author(s) -
Phan NgocMinh,
Shear Trevor A.,
Zakharov Lev N.,
Johnson Darren W.
Publication year - 2020
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.202001242
Subject(s) - thioether , chemistry , hydrocarbon , cyclophane , sulfur , disulfide bond , dynamic covalent chemistry , covalent bond , organic chemistry , stereochemistry , molecule , supramolecular chemistry , biochemistry
The union of metal‐directed self‐assembly, dynamic covalent chemistry, and sorting gives rise to 3 new unsymmetrical tetrameric disulfide macrocycles. Stepwise sulfur extrusion from the self‐assembled disulfides to, first, thioethers, and then to hydrocarbons by photochemically promoted routes, gives rise to a collection of 7 new thioether and hydrocarbon cyclophanes related to the venerable family of [ n ]paracyclophanes. These methods provide an efficient self‐assembly approach to the synthesis of hydrocarbon macrocycles (related to carbon “nanohoops”), a class of structures that are typically formed in lengthier, stepwise syntheses.