Diphenylphosphoryl azide ( DPPA ) is an organic compound . It is widely used as a reagent in the synthesis of other organic compounds.
5-501: DPPA may refer to: Diphenylphosphoryl azide Driver's Privacy Protection Act , a 1994 federal U.S. law concerning privacy of DMV information United Nations Department of Political and Peacebuilding Affairs , a department of the United Nations Secretariat Topics referred to by the same term [REDACTED] This disambiguation page lists articles associated with
10-441: A good leaving group. Finally, the acyl azide reacts in the normal manner to give the urethane. Studies show that DPPA reacts with amines giving the corresponding phosphoramidates; it therefore appears that formation of the amide similarly involves the intermediate anhydride, followed by nucleophilic substitution by the amine. In the synthesis of NSAIDs, DPPA is able to rearrange a propanoyl group into an isopropanoic acid. DPPA
15-419: Is believed to involve transfer of the azido group to the carboxylic acid. It is now suggested that this reaction proceeds through the intermediate mixed anhydride , resulting from attack by the nucleophilic carboxylate anion on the phosphorus atom, with expulsion of the azide ion. The latter then attacks the carbonyl carbon atom, to give the acyl azide and loss of the diphenylphosphate anion, known to be
20-461: The azido group by treatment with nucleophilic reagents , such as ammonia and various amines . This compound is used as a reagent for the synthesis of peptides by virtue of its reactions with carboxylic acids leading to either the urethane or the amide . The formation of the urethane is particularly valuable since it works with carboxylic acids which fail to undergo the Schmidt reaction , and
25-496: The title DPPA . If an internal link led you here, you may wish to change the link to point directly to the intended article. Retrieved from " https://en.wikipedia.org/w/index.php?title=DPPA&oldid=932801399 " Category : Disambiguation pages Hidden categories: Short description is different from Wikidata All article disambiguation pages All disambiguation pages Diphenylphosphoryl azide DPPA undergoes pseudohalogen replacement of
#473526