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[3 + 2] Cycloadditions of Nitrile Oxides to C70 Affording 4,5-Dihydroisoxazoles and Their Structure Determination

✍ Scribed by Irngartinger, Hermann ;Köhler, Claus-Markus ;Baum, Gerhard ;Fenske, Dieter

Publisher: John Wiley and Sons
Year: 1996
Tongue: English
Weight: 667 KB
Volume: 1996
Category: Article
ISSN: 0947-3440
DOI: 10.1002/jlac.199619961017

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✦ Synopsis

Abstract

Three isomeric monoadducts 2aA, 2aB, and 2aC of fullerene‐70 with 2,4,6‐trimethoxybenzonitrile oxide 1a were synthesized and isolated. With a combination of FAB‐MS, ^13^C‐ and ^1^H‐NMR spectroscopy the structure of the orientational and regioisomers could be assigned. A precise X‐ray structure analysis of the isomer 2aA with the substituent placed above the pole could be performed at low temperature (170 K). The corresponding monoadduct 3a of C~60~ was synthesized, isolated and characterized. In the same manner a mixture of three isomeric monoadducts 2b of C~70~ with ethoxycarbonylnitrile oxide 1b was obtained and characterized. The monadducts 2c of C~70~ with 9‐anthrylnitrile oxide 1c were characterized by FAB‐MS.

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