3242-56-6Relevant academic research and scientific papers
PREPARATION OF DIAZO AND DIAZONIUM COMPOUNDS
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Page/Page column 32, (2010/06/13)
A method for making diazo-compounds, diazonium salts thereof and other protected forms of these compounds. Diaz-compounds are prepared by reaction of a tertiary phosphine reagent carrying a reactive carbonyl group with an azide. The reaction can also generate an acyl triazene which can be converted thermally or by addition of base to form the diazo-compound or the acyl triazene can be isolated. The method is particularly useful for conversion of azides carrying one or more electron withdrawing groups to diazo-compounds. The method can be carried out in aqueous medium under mild conditions and is particularly useful for conversion of azido sugars to diazo-compound and diazonium salts thereof under physiological conditions. Tertiary phosphine reagents, particularly those that are water-soluble, and precursors for preparation of the reagents are provided.
Diazo transfer reaction in solid state
Ghosh,Datta
, p. 191 - 200 (2007/10/02)
A highly efficient methodology in solid state has been developed for the synthesis of α-diazocarbonyl/sulfonyl compounds from active methylene precursors using tosyl azide or 4-carboxybenzenesulfonyl azide and potassium carbonate, devoid of any aqueous work-up, save a column filtration over silica gel.
CYCLOADDITIONS OF DISUBSTITUTED DIAZO COMPOUNDS TO P-CHLORO(BISTRIMETHYLSILYL) METHYLENE PHOSPHINE.
Thoraval, J. Y.,Nagai, W.,Yeung Lam Ko, Y. Y. C.,Carrie, R.
, p. 3859 - 3868 (2007/10/02)
Disubstituted diazo compounds rapidly add to P-chloro (bistrimethylsilyl) methylene phosphine at low temperature. 1H, 31P and 13C NMR allow the characterization of the resulting cycloadducts and the establisment of the stereochemistry of the resulting cycloadducts which are potential precursors of ?3λ5 bis methylene phosphorane by nitrogen extrusion.
A Simple Procedure for Preparation of α-Diazocarbonyl Compounds
Rao, Y. Koteswar,Nagarajan, M.
, p. 735 - 737 (2007/10/02)
The use of 1,8-diazabicycloundec-7-ene as a base in Regitz reaction leads to improved yields of α-diazocarbonyl compounds in much shorter time (15 min).
REGIOSPECIFIC SYNTHESIS OF α-(PHENYLTHIO)CYCLOALKENONES AND OF α-PHENYL-α-(PHENYLTHIO)KETONES VIA αα-ADDITION OF PHENYLSULPHENYL CHLORIDE TO α-DIAZOKETONES
McKervey, M. Anthony,Ratananukul, Piniti
, p. 117 - 120 (2007/10/02)
Cyclic α-diazoketones react with phenylsulphenyl chloride at room temperature to furnish α-chloro-α-(phenylthio)cycloalkanones which undergo ready dehydrochlorination to α-(phenylthio)cycloalkenones when treated with triethylamine; acyclic, terminal α-diazoketones also furnish α-chloro-α-(phenylthio)adducts which are useful electrophiles in the synthesis of α-phenyl-α-(phenylthio)ketones.
Polymer Anchored Sulfonylazide for Deformylating Diazo Group Transfer and the Synthesis of Diazo-cyclopolyenes
Duerr, Heinz,Hauck, Gerhard,Brueck, Wolfgang,Kober, Helge
, p. 1149 - 1152 (2007/10/02)
Polymer anchored sulfonylazide is compared with its efficiency in the diazogroup transfer reaction of tosylazide.The resulting yields with the polymeric reaction are slihgtly lower than with tosylazide.However the greater thermostability of polymeric sulfonyl azide and its workup procedure make this alternative very attractive for synthesis.The reaction of polymeric sulfonyl azide with cyclic polyenes gives very small yields compared with the monomeric reaction.The attempt to generate diazocyclononatetraene by an alternative route leads only to the secondary product namely indene.At low temperature, and intermediate diazocompound is, however, observed, which is tentatively assigned to structure 12. - Key words: Polymer-bound Sulfonylazide, Azogroup Transfer, Synthesis of Diazo-cyclopolyenes
