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All 5 posts Subject: Trimethylsilylmethyl Azide: RLi or RMgX -> RNH2 Please login to post Down

Rhodium
(Chief Bee)
06-25-03 22:29
No 442538
User Picture       Trimethylsilylmethyl Azide: RLi or RMgX -> RNH2
(Rated as: good read)

Synthesis and Reactions of Trimethylsilylmethyl Azide
J. Chem. Soc. Chem. Commun. 1322 (1983) (https://www.rhodium.ws/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 15:06
No 443996
      Interesting

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 15:26
No 444000
User Picture       I like elegant functional group transformations

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 16:08
No 444009
      Cool

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 13:11
No 453724
User Picture       Azidomethyl phenyl sulfide as NH2 synthon
(Rated as: good read)

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

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	All 5 posts		Subject: Trimethylsilylmethyl Azide: RLi or RMgX -> RNH2		Please login to post		Down


		Rhodium (Chief Bee) 06-25-03 22:29 No 442538				Trimethylsilylmethyl Azide: RLi or RMgX -> RNH2 (Rated as: good read)
						Synthesis and Reactions of Trimethylsilylmethyl Azide J. Chem. Soc. Chem. Commun. 1322 (1983) (https://www.rhodium.ws/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 15:06 No 443996				Interesting
						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 15:26 No 444000				I like elegant functional group transformations
						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 16:08 No 444009				Cool
						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 13:11 No 453724				Azidomethyl phenyl sulfide as NH2 synthon (Rated as: good read)
						Azidomethyl phenyl sulfide. A synthon for NH₂ Barry M. Trost, William H. Pearson J. Am. Chem. Soc. 103(9); 2483-2485 (1981) (https://www.rhodium.ws/pdf/ph-s-ch2-n3.nh2.synthon.pdf)

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