‘Phospha-Wittig’ reactions using isolable phosphoranylidenephosphines ArP[double bond, length half m-dash]PR3 (Ar = 2,6-Mes2C6H3 or 2,4,6-But3C6H2)

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Shashin Shah and John D. Protasiewicz


Abstract

Phosphoranylidenephosphines DmpP[double bond, length half m-dash]PMe3 (1a, Dmp = 2,6-Mes2C6H3) and Mes*P[double bond, length half m-dash]PMe3 (1b, Mes* = 2,4,6-But3C6H2) act as ‘Phospha-Wittig’ reagents with aldehydes providing phosphaalkenes [ArP[double bond, length half m-dash]C(H)R] in high yields.


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