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[3 + 2] Cycloadditions of Nitrile Oxides to C 70 Affording 4,5‐Dihydroisoxazoles and Their Structure Determination
Author(s) -
Irngartinger Hermann,
Köhler ClausMarkus,
Baum Gerhard,
Fenske Dieter
Publication year - 1996
Publication title -
liebigs annalen
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0947-3440
DOI - 10.1002/jlac.199619961017
Subject(s) - chemistry , nitrile , substituent , oxide , structural isomer , spectroscopy , nuclear magnetic resonance spectroscopy , fullerene , stereochemistry , crystallography , organic chemistry , physics , quantum mechanics
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.