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New Cycloadditions of ( E )‐ N ,α‐Dimethyl‐α‐(4‐[2.2]paracylophanyl)nitrone
Author(s) -
Aly Ashraf A.,
Hopf Henning,
Ernst Ludger,
Dix Ina,
Jones Peter G.
Publication year - 2006
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.200500745
Subject(s) - chemistry , dimethyl acetylenedicarboxylate , aryne , isoxazole , nitrone , medicinal chemistry , isocyanate , pyrrole , cycloaddition , stereochemistry , organic chemistry , catalysis , polyurethane
When N ,α‐dimethyl‐α‐(4‐[2.2]paracyclophanyl)nitrone ( 1 ) is treated with dimethyl acetylenedicarboxylate ( 5 ), phenyl isocyanate ( 9 ), benzyne ( 13 ), or ethyl propiolate ( 16 ), the [2.2]paracyclophane‐based pyrrole 6 , imidazole 10 , and isoxazole derivatives 14 , 15 , and 17 are formed in good yields. The stereoisomeric benzisoxazoles 14 and 15 obtained from the reaction between 1 and benzyne ( 13 ) could be separated and the structure of one of these stereoisomers, 15 , was assigned by X‐ray structural analysis.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)