3-Diethylamino-4-(4-methoxyphenyl)-5-vinyl-isothiazole 1,1-dioxide was reacted with nitrile oxides and munchnones affording the cycloadducts in good yields. The cycloaddition reaction occurred at the vinyl group exclusively. The cycloadducts undergo pyrolytic transformation into α,β-unsaturated nitriles through the isoxazole- or pyrrole-isothiazoline 1,1-dioxide intermediates.
Isothiazoles. Part VIII. Thermal rearrangement to α,β-unsaturated nitriles of cycloadducts from 3-diethylamino-4-(4-methoxyphenyl)-5-vinyl- isothiazole 1,1-dioxide with nitrile oxides and munchnones / F. Clerici, M.L. Gelmi, R. Soave, M. Valle. - In: TETRAHEDRON. - ISSN 0040-4020. - 54:37(1998), pp. 11285-11296. [10.1016/S0040-4020(98)00668-1]
Isothiazoles. Part VIII. Thermal rearrangement to α,β-unsaturated nitriles of cycloadducts from 3-diethylamino-4-(4-methoxyphenyl)-5-vinyl- isothiazole 1,1-dioxide with nitrile oxides and munchnones
F. ClericiPrimo
;M.L. GelmiSecondo
;R. SoavePenultimo
;
1998
Abstract
3-Diethylamino-4-(4-methoxyphenyl)-5-vinyl-isothiazole 1,1-dioxide was reacted with nitrile oxides and munchnones affording the cycloadducts in good yields. The cycloaddition reaction occurred at the vinyl group exclusively. The cycloadducts undergo pyrolytic transformation into α,β-unsaturated nitriles through the isoxazole- or pyrrole-isothiazoline 1,1-dioxide intermediates.
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