Rhodium
(Chief Bee)
06-25-03 15:29
No 442538
       Trimethylsilylmethyl Azide: RLi or RMgX -> RNH2
(Rated as: good read) 		 Bookmark   

Synthesis and Reactions of Trimethylsilylmethyl Azide
J. Chem. Soc. Chem. Commun. 1322 (1983) (../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
(Active Asperger Archivist)
07-02-03 08:06
No 443996
       Interesting  Bookmark   

But what does it relate to on this site?  (I'm sure I'm simply overlooking something)
Act quickly or not at all. 		 
 
 
 
    Rhodium
(Chief Bee)
07-02-03 08:26
No 444000
       I like elegant functional group transformations  Bookmark   

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
(Active Asperger Archivist)
07-02-03 09:08
No 444009
       Cool  Bookmark   

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.
Act quickly or not at all. 		 
 
 
 
    Rhodium
(Chief Bee)
08-15-03 06:11
No 453724
       Azidomethyl phenyl sulfide as NH2 synthon
(Rated as: good read) 		 Bookmark   

Azidomethyl phenyl sulfide. A synthon for NH2
Barry M. Trost, William H. Pearson
J. Am. Chem. Soc. 103(9); 2483-2485 (1981) (../rhodium/pdf /ph-s-ch2-n3.nh2.synthon.pdf)