[peptideismylife]

Hi chemists,

I was wondering about which kind of reaction occurs between phosphites like trimethyl phosphite and azides like alkyl azides. Taking into the account the nucleophilicty of these phosphites...I guess that phosphite attack one of the electrophilic nitrogen of azide...

In case of having a phosphine....I see this reaction due to the lone pair in the P but in case of a phosphite, which it doesnt have any lone pair...I don't see it clear....

[discodermolide]

Hi chemists,

I was wondering about which kind of reaction occurs between phosphites like trimethyl phosphite and azides like alkyl azides. Taking into the account the nucleophilicty of these phosphites...I guess that phosphite attack one of the electrophilic nitrogen of azide...

In case of having a phosphine....I see this reaction due to the lone pair in the P but in case of a phosphite, which it doesnt have any lone pair...I don't see it clear....

Phosphites have lone pairs! Remember the Arbusov reaction or the Horner-Emmons reaction!

[peptideismylife]

Yeah! right now I found some literature about it!

http://users.ox.ac.uk/~mwalter/web_05/resources/phos_chem/org_phosph_chem.shtml#The%20Michaelis-Arbusov%20Reaction

But regarding to the phosphites...I would wait that phosphites are less reactive than phosphines...I mean both have lone pair at Phosphor but the presence of an oxygen in the phosphites....make less reactive the lone pair....and therefore less nucleophilic...

[discodermolide]

Yeah! right now I found some literature about it!

http://users.ox.ac.uk/~mwalter/web_05/resources/phos_chem/org_phosph_chem.shtml#The%20Michaelis-Arbusov%20Reaction

But regarding to the phosphites...I would wait that phosphites are less reactive than phosphines...I mean both have lone pair at Phosphor but the presence of an oxygen in the phosphites....make less reactive the lone pair....and therefore less nucleophilic...

Dure phosphates are less nucleophillic than phosphines. But with an electrophile like azide I doubt i.e. will make much difference.