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1,3‐Dipolar cycloadditions of cyclopentadienones with nitrile TV‐oxides
Author(s) -
Argyropoulos N. G.,
Alexandrou N. E.
Publication year - 1979
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570160424
Subject(s) - chemistry , nitrile , cycloaddition , regioselectivity , adduct , molecular orbital , 1,3 dipolar cycloaddition , structural isomer , photochemistry , computational chemistry , medicinal chemistry , stereochemistry , organic chemistry , molecule , catalysis
The cycloaddition reactions of nitrile oxides with several substituted cyclopentadienones leads to the formation of condensed mono‐isoxazolines (3α,5‐bis‐substituted‐6,6α‐diphenyl‐3α H ,4 H ,6α H ‐cyclopenta[2,3‐ d ]isoxazol‐4‐ones) and in some cases to bis‐isoxazoline derivatives as minor products. The cycloaddition to mono‐adducts is regioselective and only one regioisomer is formed, which can be predicted after consideration of the frontier molecular orbitals of the reacting species. The spectral data of the isoxazolines 3–7 are examined, whereas their structure was fully characterized by X‐ray analysis.