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DOI: 10.1039/A904422A (Paper) Reference Section for: Chem. Commun., 1999, 1423-1424

Unexpected [2 + 2] cycloaddition between the P[double bond, length half m-dash]O group of P-(2,4,6-triisopropylphenyl) P-heterocycles and dimethyl acetylenedicarboxylate

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György Keglevich, Henrietta Forintos, Áron Szöllõsy and László Tõke

Abstract

The reaction of 1-(2,4,6-triisopropylphenyl)-1,2-dihydrophosphinine 1-oxide 1d with dimethyl acetylenedicarboxylate (DMAD) affords, surprisingly, oxaphosphetene 3 instead of the expected Diels–Alder cycloadduct; the unusual reactivity of the trialkylphenylphosphine oxides towards DMAD seems to be of general value.

References

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  9. Selected data for 3: δC(CDCl3) 16.2 (JPC 17.5, C6–Me), 23.5 (JPC 8.7, o-CH(CH3)2), 25.3 (p-CH(CH3)2), 30.0 (JPC 62.8, C9), 31.8 (JPC 6.7, o-CHMe2), 34.0 (p-CHMe2), 50.6 (CH3O), 51.5 (CH3O), 74.4 (JPC 107.4, C3), 119.3 (JPC 13.7, C8), 121.6 (JPC 94.3, C1′), 122.5 (JPC 85.0, C5), 123.2 (JPC 11.9, C3′), 140.0 (JPC 14.1, C7), 152.7 (JPC 11.3, C2′), 153.0 (C4′), 155.4 (JPC 14.8, C6), 166.4 (JPC 14.8, C[double bond, length as m-dash]O), 167.5 (JPC 15.6, C[double bond, length as m-dash]O), 182.4 (JPC 6.1, C4).
  10. Selected data for 5-1: δP(CDCl3) 23.9 (69%), 5-2: δP(CDCl3) 29.1 (31%).
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  12. Selected data for 7: δP(CDCl3) 39.5; δC(CDCl3) 20.7 (JPC 18.0, C6-Me), 23.8 (JPC 5.9, o-CH(CH3)2), 25.5 (p-CH(CH3)2), 26.0 (JPC 59.2, C8), 32.0 (JPC 6.3, o-CHMe2), 34.3 (p-CHMe2), 35.7 (JPC 6.8, C7), 50.7 (CH3O), 51.8 (CH3O), 76.1 (JPC 103.0, C3), 116.3 (JPC 88.6, C5), 122.8 (JPC 93.7, C1′), 123.2 (JPC 11.3, C3′), 152.7 (C2′), 152.8 (C4′), 164.0 (JPC 23.0, C6), 167.0 (JPC 14.3, C[double bond, length as m-dash]O), 168.1 (JPC 15.4, C[double bond, length as m-dash]O), 182.5 (JPC 6.2, C4).
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