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Synthesis of Azides

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p-Toluenesulfonyl Azide - Paperplane

Upon treatment with sulfonyl azides, a variety of Grignard reagents or enolates may be converted into azides or amines. A significant side reaction that occurs under these conditions is the diazo transfer reaction: instead of fragmenting into an azide and sulfinic acid, the intermediate triazene salt may break down to a diazo compound and sulfonamide. Changing workup conditions may favor one product over another. In general, for reactions of enolates substituted with Evans oxazolidinones, trifluoroacetic acid promotes diazo transfer while acetic acid encourages azidation (the reasons why are unclear). Solvent and the enolate counterion also influence the observed ratio of diazo to azide products.

Tosyl (Ts) group is commonly used as a protecting group for amines in organic synthesis
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The reactions of aryl and heteroaryl hydrazides with tosyl azide in the presence of NaOH under phase-transfer conditions give rise to the corresponding aromatic and heteroaromatic compounds (eq 15). After oxidative workup, reactions with trialkylboranes yield alkyl aryl sulfides (eq 16).

Tosyl azide acts as a transfer ..

Previous message: Ohad Ilovich: "Re: ORGLIST: Synthesis of Trisyl azide" Hello Everybody, I'm looking for Chiral GC columns. But I am unable to find out its source or
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The most synthetically useful aminations of enolate anions employ -acyloxazolidinone substrates.. The chiral auxilliaries on these compounds are easily removed after hydrazine formation (with azo compounds) or azidation (with trisyl azide). Azidation using the latter reagent is more efficient than bromination followed by nucleophilic substitution by the azide anion Palladium on carbon and hydrogen gas reduce both azide and hydrazide products (the latter only after conversion to the hydrazine).

Additions across pi bonds appear to proceed by typical nucleophilic addition pathways in most cases. Alkyl-, aryl-, and heteroaryllithium reagents add to azides to afford triazene salts. Reduction of these salts leads to amines, although they also may be converted to azides upon acidic workup with overall elimination of sulfinic acid.

Thieme E-Journals - Synthesis / Full Text

12/07/2010 · ChemInform Abstract: Asymmetric Synthesis of Unsaturated Monocyclic and ..
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readily prepared by treatment of the commercially available triisopropylbenzenesulfonyl chloride (trisyl chloride) with sodium azide.

30/05/2007 · Convenient Synthesis of Dialkyl 1‐Azidoalkylphosphonates using Tetramethylguanidinium Azide as Azidation Agent
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  • 2,4,6-Triisopropylbenzenesulfonyl Azide

    Tosyl - Wikipedia

  • 2,4,6-Triisopropylbenzenesulfonyl Azide 1 ..

    Most common amine protection methods Tosyl chloride and pyridine in dichloromethane Most ..

  • the trisyl azide in these conversions ..

    p-Toluenesulfonyl Azide 1 ..

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