Azide reagent

The polymer (SN)x may also be made in a two-step process using azide reagents. Thus the reaction of S2CI2 with sodium azide in... 

The use of azide reagents is also important for the synthesis of cyclic sulfur(VI)-nitrogen systems. The reaction of SOCI2 with sodium azide in acetonitrile at -35°C provides a convenient preparation of the trimeric sulfanuric chloride [NS(0)C1]3 (Eq. 2.16). " Thionyl azide, SO(N3)2 is generated by the heterogeneous reaction of thionyl chloride vapour with silver azide (Eq. 2.17). This thermally unstable gas was characterized in situ by photoelectron spectroscopy. The phenyl derivative of the six-membered ring [NS(0)Ph]3 can be prepared from lithium azide and PhS(0)Cl. ... 

The phenyl azide reagent should be stored in the cold and distilled on the day it is used in order to minimize extraneous color formation. 

The impure compound, present as a majority in the distillation residue from preparation of 1-diazoindene, will explode if the bath temperature exceeds 120°C [1], A polymer-bound sulfonyl azide reagent has been described as safer in use than the title compound [2], Distillation of the azide at 130-132 C/ 0.5 mbar from an oil bath at 145°C led to darkening, then violent explosion of the 30-40% residue [3],... 

To complete the synthesis of the diazofluorene, the cyclization product 126 is treated with diisopropylethylamine and triflyl azide [50], to afford the diazofluorene 127 in 81 % yield. Under these conditions, the hydroxyfulvene is likely deprotonated to generate a cyclopentadienyl anion. Attack of this anion on the trifyl azide reagent... 

Ti(OPr )2(N3)2 can be prepared in situ by stirring a mixture of Ti(OPri)4+2 equivalents of Me3SiN3 in benzene under Ar or N2 for 5 hours until the solution becomes clear. A C-3 selective azide reagent consisting of NaN3 supported on a calcium zeolite has also been reported. Onaka, M. Sugita, K. Izumi, Y. Chem, Lett. 1986, 1327. 

Hassner et al. (15) explored the synthetic utility of the polymeric azidation reagent 63 to prepare di- and tri-azidomethanes 64 and 66 at ambient temperature. They also studied the intermolecular cycloaddition of these azides with dimethyl acetylenedicarboxylate (DMAD) to yield the corresponding cycloadducts... 

Kudzin ZH, Kotynski A, Kielbasinski P. 1991. Application of the iodine-azide reagent for selective detection of thiophosphoryl compounds in thin-layer chromatography. J Chromatogr 588 307-313. 

Mix a drop of the test solution and a drop of the iodine-azide reagent on a watch glass. A vigorous evolution of bubbles (nitrogen) ensues. 

Thiosulphates and thiocyanates act similarly and must therefore be absent. The sulphide can, however, be separated by precipitation with zinc or cadmium carbonate. The precipitated sulphide may then be introduced, say, at the end of a platinum wire into a semimicro test-tube or centrifuge tube containing the iodine-azide reagent, when the evolution of nitrogen will be seen. 

The importance of a-diazo ketones as synthetic intermediates has led to the development of a number of general methods for their preparation.5 Particularly popular approaches include the acylation of diazo alkanes and the base-catalyzed "diazo group transfer" reaction of sulfonyl azides with 8-dicarbonyl compounds.6-7 While direct diazo transfer to ketone enolates is usually not a feasible process,8-9 diazo transfer to simple ketones can be achieved in two steps by employing an indirect deformylative diazo transfer strategy in which the ketone is first formylated under Claisen condensation conditions, and then treated with a sulfonyl azide reagent such as p-toluenesulfonyl azide.6a,6c,9,i0,11... 

For the azide cleavage of chiral 2,3-epoxy diester 3, the submitter s earlier procedure81 was modified to reduce the amount of azide reagent (azidotrimethylsilane, TMSN3) and lower the reaction temperature. This effort, coupled with the submitter s recent finding that such a reaction can be accelerated in the presence of amines,89,9 led to the use of the system described above. The reaction may proceed by way of the... 

In 2006, two groups independently reported the novel asymmetric synthesis of tamiflu (106). Corey et al. reported a short enantioselective pathway for the synthesis of 106 from 1,3-butadi-ene and acrylic acid shown in O Scheme 22 [ 111 ]. The key steps of the synthesis are (1) Diels-Alder reaction of 1,3-butadiene (146) and trifluoroethyl acrylate (147) in the presence of chiral ligand 148 developed in the laboratory [112], (2) the introduction of two amino groups in tamiflu (106) without using potentially hazardous and explosive azide reagents, and (3) a novel S nBr4 - catalyzed bromoacetamidation. 

Benati, L., Calestani, G., Nanni, D., Spagnolo, P. Reactions of Benzocyclic 3-Keto Esters with Tosyl and 4-Nitrophenyl Azide. Structural Influence of Dicarbonyl Substrate and Azide Reagent on Distribution of Diazo, Azide and Ring-Contraction Products. J. Org. Chem. 1998, 63, 4679-4684. 

Addition of hydrazines to 1,3-difunctional compounds is one of the most common methods employed for the preparation of pyrazoles. For example, several synthesis of pyrazoles have been reported where azide reagents are added to a,P-unsaturated systems. Reactions of trifluoroacetyl enol ether (thiophene) 1 with hydrazines afforded 3-(2-furyl) or 3-(2-thienyl)pyrazoles 2 <05S2744>. A regiospecific one-pot synthesis of trifluoromethyl-substituted heteroaryl pyrazolyl ketones has also been disclosed <05JHC631, 05JHC1055>. 1,3,5-... 

Diones and 1,3-dihalides can also be utilized as substrates for azide reagents in the preparation of pyrazoles. Primary aliphatic and aromatic amines 13 underwent electrophilic amination with oxaziridine 14 to give the corresponding A-Boc hydrazines which reacted further... 

Other metal-mediated reactions of azide reagents to terminal alkynes have also been reported. Indium(ll) triflate catalyzed tandem azidation/l,3-dipolar cycloaddition of various (o,(o-dialkoxyalkynes 134 with trimethylsilyl azide yielded fused 1,2,3-triazoles 135 <05TL8639>. A new ruthenium-catalyzed process for the regioselective synthesis of 1,5-disubstituted-1,2,3-triazoles has been developed <05JA15998>. 

A s3mthesis of 4-substituted 1,2,3-triazoles involves reaction of 1-alkynes with diorgano-aluminum azides. The inexpensive and nontoxic azide reagents are available from mixing R2AICI with NaN3 in toluene. ... 

Starting Molecule d-/so-Lysergic acid azide Reagent Diethylamine... 

Starting Molecule d-iso-Lysergic acid azide Reagent d-2-Aminobutanol-1... 

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