The Vespiary

The Hive => Novel Discourse => Topic started by: Rhodium on June 25, 2003, 03:29:00 PM

Title: Trimethylsilylmethyl Azide: RLi or RMgX -> RNH2
Post by: 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)

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

(https://www.thevespiary.org/rhodium/Rhodium/hive/hiveboard/picproxie_docs/000442538-file_zjdg.gif)

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.

Title: Interesting
Post by: Aurelius 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)

Title: I like elegant functional group transformations
Post by: Rhodium 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.

Title: Cool
Post by: Aurelius 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.

Title: Azidomethyl phenyl sulfide as NH2 synthon
Post by: Rhodium 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)

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

(https://www.thevespiary.org/rhodium/Rhodium/hive/hiveboard/picproxie_docs/000442538-file_emqm.gif)