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[2.2]Paracyclophane‐Bis(triazole) Systems: Synthesis and Photochemical Behavior
Author(s) -
Bahrin Lucian G.,
Sarbu Laura G.,
Jones Peter G.,
Birsa Lucian M.,
Hopf Henning
Publication year - 2017
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201701593
Subject(s) - adduct , intramolecular force , chemistry , reactivity (psychology) , photochemistry , triazole , combinatorial chemistry , stereochemistry , organic chemistry , medicine , alternative medicine , pathology
Mono‐, pseudo‐gem , and pseudo‐para ethynylcyclophanes and bis(azides) have been employed as addition partners in CuAAC reactions to design and build complex extended molecular scaffolds. The reactivity of the resulting triazoles was investigated under photochemical conditions. A variety of newly substituted [2.2]paracyclophanes were identified; deazotization of pseudo‐gem and pseudo‐para adducts provided indolophane derivatives. An intramolecular stabilization effect was observed in the case of pseudo‐gem derivatives. A photochemical rearrangement from a pseudo‐para adduct to a pseudo‐ortho product was identified.