Synthesis and Reactions of Trimethylsilylmethyl Azide

J. Chem. Soc. Chem. Commun. 1322 (1983)

(https://www.thevespiary.org/rhodium/Rhodium/pdf/trimethylsilylmethylazide.grignard.amination.pdf)

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Abstract

Trimethylsilylmethyl Azide (TMSMA / Me₃Si-CH₂N₃), which is prepared in quantitative yield from Trimethylsilylmethyl Chloride and Sodium Azide, can be used to aminate aryl-lithiums or aryl Grignard reagents.

But what does it relate to on this site?  (I'm sure I'm simply overlooking something)

It might be a way of turning bromosafrole to MDA, or phenethylbromides to PEAs for example - even if there are no actual examples of aliphatic grignards in the article, it doesn't say its impossible either.

That's great.  I just figured you weren't considering that b/c they only specify aromatic functionalities.  that would be cool if it worked on aliphatics though.

Azidomethyl phenyl sulfide. A synthon for NH₂
Barry M. Trost, William H. Pearson

J. Am. Chem. Soc. 103(9); 2483-2485 (1981)

(https://www.thevespiary.org/rhodium/Rhodium/pdf/ph-s-ch2-n3.nh2.synthon.pdf)

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