Diels–Alder reaction
10 real reactions from the literature, on α,β-unsaturated ketones, conjugated dienes, cyclic conjugated dienes and quinones. Each scheme shows starting materials, conditions and products, with the yield and reference where the source reports them.
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Diels–Alder: 1,3-butadiene (a conjugated diene) and maleic anhydride (an α,β-unsaturated ester) with benzene gives tetrahydrophthalic anhydride (the cyclohexene adduct).
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Diels–Alder: 2-cyclopenten-1-one (an α,β-unsaturated ketone) and 1,3-cyclohexadiene (a cyclic conjugated diene) gives the cyclohexene adduct. 66% yield.
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Diels–Alder: 3-methyl-4-oxo-2-pentenoic acid (an α,β-unsaturated ketone) with SnCl4; 25 C gives the cyclohexene adduct. 73% yield.
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Diels–Alder: 1,4-benzoquinone with 25 C, 2 weeks gives the cyclohexene adduct. 93% yield.
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Diels–Alder: methyl 1H-pyrrole-1-carboxylate (a heteroarene) and ethynyl p-tolyl sulfone (a terminal alkyne) with 80 C gives the cyclohexene adduct. 36% yield.
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Diels–Alder: an α,β-unsaturated ketone gives the cyclohexene adduct. 59% yield, mixture of 3 diastereomers yield.
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Diels–Alder: cyclobutenone (an α,β-unsaturated ketone) with ZnCl2 gives the cyclohexene adduct. 86% yield.
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Diels–Alder: 2-methoxy-5-methyl-1,4-benzoquinone with 100 C gives the cyclohexene adduct. 86% yield.
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Diels–Alder: a conjugated diene with 300 C gives the cyclohexene adduct and the cyclohexene adduct. regioisomer 2: 23% yield.
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Diels–Alder: a cyclic conjugated diene and methyl (2E)-3-methyl-4-oxo-2-butenoate (an α,β-unsaturated ester) with 100 C gives the cyclohexene adduct. 61% yield.