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methylenetriphenylphosphorane : ウィキペディア英語版
methylenetriphenylphosphorane

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Methylenetriphenylphosphorane is an organophosphorus compound with the formula Ph3PCH2. It is the parent member of the phosphorus ylides, popularly known as Wittig reagents. It is a highly polar, highly basic species.
==Preparation and use==
Methylenetriphenylphosphorane is prepared from triphenylphosphine and methyl bromide followed by deprotonation of the resulting phosphonium salt using a strong base like butyllithium:
:Ph3PCH3Br + BuLi → Ph3PCH2 + LiBr + BuH
The compound is generally not isolated, instead it is used in situ.
Methylenetriphenylphosphorane is used to replace oxygen centres in aldehydes and ketones with a methylene group:
:R2CO + Ph3PCH2 → R2C=CH2 + Ph3PO
The phosphorus-containing product is triphenylphosphine oxide.

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