Author Topic: Trimethylsilylmethyl Azide: RLi or RMgX -> RNH2 (Read 2903 times)

Rhodium · « **on:** June 25, 2003, 03:29:00 PM »

Synthesis and Reactions of Trimethylsilylmethyl Azide

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

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

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.

Aurelius · « **Reply #1 on:** July 02, 2003, 08:06:00 AM »

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

Rhodium · « **Reply #2 on:** July 02, 2003, 08:26:00 AM »

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.

Aurelius · « **Reply #3 on:** July 02, 2003, 09:08:00 AM »

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.

Rhodium · « **Reply #4 on:** August 15, 2003, 06:11:00 AM »

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)

News:

Author Topic: Trimethylsilylmethyl Azide: RLi or RMgX -> RNH2 (Read 2903 times)

Rhodium

Trimethylsilylmethyl Azide: RLi or RMgX -> RNH2

Aurelius

Interesting

Rhodium

I like elegant functional group transformations

Aurelius

Cool

Rhodium

Azidomethyl phenyl sulfide as NH2 synthon