Use of an 18O-labelled phosphonamidic-sulfonic anhydride to learn more about the mechanism by which O-sulfonyl-N-phosphinoylhydroxylamines rearrange
Author:
Publisher
Royal Society of Chemistry (RSC)
Subject
Organic Chemistry,Physical and Theoretical Chemistry,Biochemistry
Link
http://pubs.rsc.org/en/content/articlepdf/2006/OB/B603051C
Reference11 articles.
1. Preparation and characterisation of N-(diphenylphosphinoyl)hydroxylamine, and conversion into O-sulphonyl derivatives that undergo Lossen-like rearrangement
2. N-(alkylphenylphosphinoyl)hydroxylamines: highly selective migration of the phenyl group in the base-induced rearrangement of their O-methylsulphonyl derivatives
3. Rearrangement reactions of N-phosphinoyl-O-sulphonylhydroxylamines with amines under competitive conditions. Possible involvement of monomeric metaphosphonimidates and phosphonamidic sulphonic mixed anhydrides
4. Stereospecificity in the rearrangement reactions of an N-phosphinoyl-O-sulfonylhydroxylamine with methylamine and tert-butylamine: retention of configuration at phosphorus as evidence for the initial formation of a phosphonamidic sulfonic mixed anhydride
5. Competing sulfonylation and phosphonylation following rearrangement of an O-sulfonyl-N-phosphinoylhydroxylamine with tert-butylamine: demonstration of a phosphonamidic-sulfonic anhydride intermediate and 18O-labelling evidence on how it may be formed1
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1. Rearrangements of Hydroxylamines, Oximes and Hydroxamic Acids;PATAI'S Chemistry of Functional Groups;2010-04-15
2. Reaction mechanisms : Part (iii) Polar reactions;Annual Reports Section "B" (Organic Chemistry);2008
3. Scrambling of the label in a fluorenylphosphonamidic [18O]-sulfonate during dissociative nucleophilic substitution (elimination–addition): a measure of the importance of preassociation;Org. Biomol. Chem.;2006
4. Quinquevalent phosphorus acids;Organophosphorus Chemistry
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