Investigations on diazo compounds and azides- LXII.: Synthesis and reactions of a-diazo phosphonates with a conjugated 1,3-diene unit |
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Authors: | Wolfgang Theis Manfred Regitz |
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Affiliation: | Department of Chemistry, University of Kaiserslautern, Erwin-Schrödinger-Straße, D-6750 Kaiserslautem Federal Republic of Germany |
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Abstract: | α-Diazo phosphonates with a conjugated 1,3-diene unit are synthesised by the Bamford-Stevens reaction ( →→). They undergo [4+2]-cycloadditions with the dienophile to form the tetrahydrotriazolopyridazines , which possess an unchanged diazo group. In contrast, dimethyl acetylenedicarboxylate () reacts exclusively with the diazo dipole of to yield the 3H-pyrazoles , which rearrange to by sigmatropic PO-shifts and hydrolyse to form . The diazo compound isomerises to the pyrazole when heated in benzene. |
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