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A Simple Route to a Pyridinyl[2.2]paracyclophane
Author(s) -
Hopf Henning,
Aly Ashraf A.,
Swaminathan Vijay Narayanan,
Ernst Ludger,
Dix Ina,
Jones Peter G.
Publication year - 2005
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.200400633
Subject(s) - chemistry , nitrone , condensation , hydrochloride , condensation reaction , stereochemistry , medicinal chemistry , organic chemistry , computational chemistry , cycloaddition , catalysis , physics , thermodynamics
4‐Acetyl[2.2]paracyclophane ( 1 ) is converted into the nitrone 2 by treatment with N ‐methylhydroxylamine·hydrochloride. When 2 is reacted with ( E )‐1,2‐dibenzoylethene ( 4 ) the pyridinyl[2.2]paracyclophane 13 is formed in a novel condensation reaction. The structures of 2 and 13 , and the mechanism of formation of the latter are discussed. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)