Phosphorous as a Nucleophile

Some assorted reactions to show the versatility of phosphorus and to exemplify the points made on page 1.


i. Shows the potency of P=O as a driving force – in the penultimate step a carbanion is created (fairly unstable) while the P=O is formed.

ii. Ph-CH2 is the only possible carbanion is the system with any stabilisation (see below), so it is the one created in the penultimate step.


i. Note the nucleophilicity of Ph3P: – able to attack and abstract Br+ from CBr4 – usually fairly inert.

ii. P=O driving force involved in the third step.

iii. The use of zinc is similar to its use in the Reformatsky Reaction (nothing to do with Phosphorus, but useful for comparison):

3.Phosphines: (“P“)