Tetrahedron p. 2755 - 2760 (1987)
Update date:2022-08-02
Topics:
Baccolini, Graziano
Dalpozzo, Renato
Errani, Ermanno
The reaction between arylhydrazones and PCl3 can give both diazaphospholes and indoles, via a common hypothetical diazaphospholine intermediate.The product ratio depends on the reaction conditions.In particular when a solvent which dissolves the phosphorus adducts is employed, indole is the almost exclusive reaction product.A mechanism is suggested for the whole indolization reaction.It involves an acid promoted cleavage of the P-N bond of the diazaphospholine to give intermediates similar to those of the accepted Fischer indolization mechanism, where the dichlorophosphino group, substituting a hydrogen atom should have an important ro le in promoting of the loss of the amino group in the last stage of the reaction, via a "Wittig-like" elimination of Cl2PNH2.
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