ChemInform Abstract: Regioselectivity of the Condensation of Stabilized Phosphoylids with 3‐Substituted Phthalic Anhydrides.

Breau, Livain; Kayser, Margaret M.

doi:10.1002/chin.198936091

ChemInform

1989

DOI: 10.1002/chin.198936091

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ChemInform Abstract: Regioselectivity of the Condensation of Stabilized Phosphoylids with 3‐Substituted Phthalic Anhydrides.

Livain Breau

Margaret M. Kayser

Abstract: Condensation of the stabilized phosphorane (IV) with various 3‐substituted phthalic anhydrides such as (I) or (V) are investigated.

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On the regioselectivity of the condensation of stabilized phosphoylids with 3-substituted phthalic anhydrides

Breau¹,

Kayser²

1989

Can. J. Chem.

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Condensations of stabilized phosphorane 1 with 3-substituted phthalic anhydrides were investigated. The importance of various effects influencing regio-and stereoselectivity of these reactions is discussed. It is proposed that the oxygen atom on the substituents in position 3 can act as aLewis base toward the electron-deficient phosphorus of the ylid. The resulting complexation stabilizes the transition state for the reaction at the ortho carbonyl group, thus offsetting the usual steric and "push effects, which favour attack at the meta carbonyl function.

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On the regioselectivity of the condensation of stabilized phosphoylids with 3-substituted phthalic anhydrides

Breau¹,

Kayser²

1989

Can. J. Chem.

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ChemInform Abstract: Regioselectivity of the Condensation of Stabilized Phosphoylids with 3‐Substituted Phthalic Anhydrides.

Abstract: Condensation of the stabilized phosphorane (IV) with various 3‐substituted phthalic anhydrides such as (I) or (V) are investigated.

Cited by 1 publication

References 1 publication

On the regioselectivity of the condensation of stabilized phosphoylids with 3-substituted phthalic anhydrides

On the regioselectivity of the condensation of stabilized phosphoylids with 3-substituted phthalic anhydrides

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