Monatshefte fur Chemie p. 553 - 564 (1994)
Update date:2022-07-31
Topics:
Fisera, L.
Sauter, F.
Froehlich, J.
Feng, Y.
Ertl, P.
Mereiter, K.
A series of spiro-substituted isoxazole derivatives were synthesized by 1,3-dipolar cycloadditions of nitrile oxides and nitrones to 4,4-methylene-1-methylpiperidine.Since nmr studies confirmed that only one regioisomer was formed selectively, semi-empirical quantum mechanical methods (AM1) were used to rationalize this regiochemical preference via calculation and inspection of HOMO-LUMO-energy and coefficients.X-ray structure analysis carried out for one of these products showed the occurrence of only one stereoisomer, explicable by comparing AM1-calculated ΔHf-values of all possible cycloadducts. - Keywords: 1,3-Dipolar cycloaddition; Nitrile oxide; Nitrone; 4,4-Methylene-1-methylpiperidine; AM1 calculations.
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Doi:10.1039/c39940001177
(1994)Doi:10.1021/om500104w
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