5456-33-7Relevant articles and documents
Staudinger’s phosphazene as an efficient esterifying reagent
Dinesh, Murugan,Ranganathan, Raja,Archana, Sivasubramaniyan,Sathishkumar, Murugan,Roshan Banu, Mohamed Sulthan,Ponnuswamy, Alagusundaram
supporting information, p. 1454 - 1460 (2016/09/14)
A new application of Staudinger’s phosphazene as an efficient esterifying reagent is reported. Staudinger’s phosphazene formed in situ by the reaction of organic mono-azide with triphenylphosphine, which is trapped by carboxylic acid, to afford amide exclusively. In contrast, interestingly the same phosphazene behaves in a different way as an efficient esterifying reagent, affording ester under a solvent-free microwave-assisted protocol wherein alcohol is added as the another component in addition to the other reactants. This discovery adds yet another new application of Staudinger’s phosphazene to synthetic chemistry.
Bis azide-triphenylphosphine as a reagent for esterification at room temperature
Dinesh, Murugan,Archana, Sivasubramaniyan,Ranganathan, Raja,Sathishkumar, Murugan,Ponnuswamy, Alagusundaram
supporting information, p. 6975 - 6979 (2015/11/27)
Modified Staudinger reaction is a well-established reaction for the amide synthesis from organic azides and carboxylic acids in the presence of phosphorous reagents. In contrary to this, it is notable that bis azide in the presence of triethylphosphite or trimethylphosphite does not afford the expected bis amides but affords the ethyl or methyl esters of the carboxylic acids respectively. This serendipitous observation when further investigated results in the discovery of bis azide-triphenylphosphine as an efficient reagent for esterification at room temperature.
Electrochemical generation and reactions of acyloxytriphenylphosphonium ions
Ohmori, Hidenobu,Maeda, Hatsuo,Kikuoka, Masayuki,Maki, Toshihide,Masui, Masaichiro
, p. 767 - 776 (2007/10/02)
Constant-current electrolysis, in an undivided cell, of Ph3P in the presence of a carboxylic acid in CH2Cl2 containing 2,6-lutidinium perchlorate as the supporting electrolyte was shown to generate the corresponding acyloxyphosphonium ion, Ph3P+-OCOR, which was converted in situ to esters, amides, and β-lactams under mild conditions.
Unusual Reaction of 6-Nitrobenzotriazolyl Carboxylates with Grignard Reagents
Okawara, Tadashi,Ikeda, Norihiro,Yamasaki, Tetsuo,Furukawa, Mitsuru
, p. 42 - 43 (2007/10/02)
The reaction of 6-nitrobenzotriazolyl carboxylates with Grignard reagents afforded various carboxylates in fairly good yields.
