Hive Novel Discourse

	Main Index Search Register Login Who's Online FAQ Links
	Main Index Search Register Login Who's Online FAQ Links

	1 Online, 0 Active		You are not logged in

This is a historical archiveThe forum is read-only. Private information has been removed. It is not possible to login.

	Novel Discourse

All 2 posts Subject: titanium (IV) isoperoxide for large scale? Please login to post Down

tropine
(Stranger)
10-01-03 14:55
No 462083
      titanium (IV) isoperoxide for large scale?

If one were to want to aminate a mole of ketone, how much titanium (IV) would they use? It looks to be a catalyst of sorts, but all write ups so far claim that double the molar ratio of ketone to titanium (IV) is used (ie 10 mmol of ketone and 20 mmol (5.9 mL) of titanium). I doubt that one would use 600 mL of titanium (IV) for the 1 mole of ketone!

Rhodium
(Chief Bee)
10-01-03 18:35
No 462109
User Picture       Reductive Amination w/ Titanium(IV)Isopropoxide
(Rated as: excellent)

You need as many moles of Ti⁴⁺ as the number of moles of methylamine added, as they bind to each other in a 1:1 fashion. This complex then in turn adds to the ketone forming a so-called (methylamino)carbinolatotitanium(IV) complex as an intermediate which is reduced either directly or via transient iminium species.

See the following articles for details:

Reductive Alkylations of Dimethylamine Using Titanium(IV)Isopropoxide and Sodium Borohydride:
An Efficient, Safe, and Convenient Method for the Synthesis of N,N-Dimethylated Tertiary Amines
Sukanta Bhattacharyya
J. Org. Chem. 60, 4928-4929 (1995) (https://www.rhodium.ws/pdf/redamin.nabh4-ti4-me2nh.pdf)

A New Method for the Synthesis of alpha-Substituted Phenethylamines via Titanium Amide Complexes
Synthesis 238-240 (1988) (https://www.rhodium.ws/pdf/titanium.amide.amphetamines.pdf)

	https://the-hive.archive.erowid.org	the-hive@erowid.org



Powdered by Not Enough Money^TM Release 6.16.4, 2022, Offensive Products Incorporated Asia
Links Erowid Rhodium

	All 2 posts		Subject: titanium (IV) isoperoxide for large scale?		Please login to post		Down


		tropine (Stranger) 10-01-03 14:55 No 462083				titanium (IV) isoperoxide for large scale?
						If one were to want to aminate a mole of ketone, how much titanium (IV) would they use? It looks to be a catalyst of sorts, but all write ups so far claim that double the molar ratio of ketone to titanium (IV) is used (ie 10 mmol of ketone and 20 mmol (5.9 mL) of titanium). I doubt that one would use 600 mL of titanium (IV) for the 1 mole of ketone!



		Rhodium (Chief Bee) 10-01-03 18:35 No 462109				Reductive Amination w/ Titanium(IV)Isopropoxide (Rated as: excellent)
						You need as many moles of Ti⁴⁺ as the number of moles of methylamine added, as they bind to each other in a 1:1 fashion. This complex then in turn adds to the ketone forming a so-called (methylamino)carbinolatotitanium(IV) complex as an intermediate which is reduced either directly or via transient iminium species. See the following articles for details: Reductive Alkylations of Dimethylamine Using Titanium(IV)Isopropoxide and Sodium Borohydride: An Efficient, Safe, and Convenient Method for the Synthesis of N,N-Dimethylated Tertiary Amines Sukanta Bhattacharyya J. Org. Chem. 60, 4928-4929 (1995) (https://www.rhodium.ws/pdf/redamin.nabh4-ti4-me2nh.pdf) A New Method for the Synthesis of alpha-Substituted Phenethylamines via Titanium Amide Complexes Synthesis 238-240 (1988) (https://www.rhodium.ws/pdf/titanium.amide.amphetamines.pdf)

All 2 posts	End of thread	Top