I've done some amount of searching and can't seem to find any evidence in the literature that there exists a phosphine analogue of carboxyl amides. I'm looking for compounds of the form $ \ce{ R(C=O)PR_{2}} $; basically a moeity similar to a primary or secondy amide but with a phosphorous atom instead of a nitrogen.

I would also wonder what the proper name for these functionalities would be. Taking a shot in the dark I might guess "phosphomide", "acyl phosphine", or "acyl phosphinide".

I would like to specifically disqualify Acyl-phosphine oxides or any compounds where the acyl-connected phosphorous is also connected to an oxygen.


When I saw this question, I realized I couldn't remember ever seeing an acylphosphine, but I was curious and went looking. I found that they're actually quite easy to make. One common thing I saw was the use of trimethylsilylphosphines with acyl chlorides to form acylphosphines.

The easier method, however, was simply to react a substituted phosphine in the presence of triethylamine with an acyl chloride. The analogous reaction can be done with amines to form amides. In this paper, they describe the synthesis of P-acetyldiphenylphosphine using diphenylphosphine, triethylamine and acetyl chloride. They have some other examples in there, but this suggests that these compounds are typically fairly trivial to synthesize.

One more note: In my searches, I saw "acylphosphine," "acyl phosphide," and "phosphomide" as named. The paper I linked uses the term "phosphomide."


Your Answer

By clicking “Post Your Answer”, you agree to our terms of service, privacy policy and cookie policy

Not the answer you're looking for? Browse other questions tagged or ask your own question.