For example, which is more likely to oxidise to the equivalent phosphate, triethylphosphite or tris(2,2,2-trifluoroethyl)phosphite?
hi, Jacob Johnston , There is no effect of electron withdrawing group on formation of phosphate from phosphite, because phosphate from phosphite formed by moisture content in environment, so u have to keep phosphite in moisture free condition.
In other side if EWG is present it will stabilize the phosphite , because it withdraw electron, as compared to EDG which donate electron and make oxygen and phoaphorus of phosphite more nucleophilic to except hydrogen and oxygen from environment.
may this ans is helpful for you.
Thank you,
@Amravati Singh wouldn't electron donating groups make the oxygen in phosphite more nucleophilic meaning the P is more negative and thus less likely to oxidise? Would have thought electron withdrawing groups, by making the P centre more positive would mean it's more liable to oxidation?
@Jacob Johnston its the negative positive effect of any element, like oxygen nitrogen phosphorus. Negative charge attract towards positive charge. If donating group is there its effect on neighboring group and its make nucleophilic site, which attract positive charge group. vice versa
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