Monatshefte fur Chemie p. 909 - 920 (1980)
Update date:2022-08-02
Topics:
Fisera, L.
Kovac, J.
Poliacikova, J.
Lesko, J.
A frontier orbital treatment of furan suggests its possible reactivity in 1,3-dipolar cycloadditions with dipoles posessing low lying LUMO's, such as nitrones, especially those with electronwithdrawing substituents.By the reaction of C-benzoyl-N-phenylnitrone 1a with an excess of furan at 60 deg C the monocycloadduct 2a, two biscycloadducts 4 and 5 and further reaction products of nitrone such as azoxybenzene 8, diketoamide 9a, benzoanilide 10a, benzoic acid 11a and phenyl glyoxylic acid 12 were isolated.The cycloaddition of C-(4-bromobenzoyl)-N-phenylnitrone 1b with furan is also reported. - Keywords: Cycloaddition of nitrone; 1,3-Dipolar cycloaddition; Frontier orbital treatment; Furan
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