tropine (Newbee)
12-15-03 06:40
No 476995
      How to reduce C=C to C-C     

Thiking of using Li in ammonia to reduce the double bond in 2,5-dimethoxy-2,5 dihydrofuran, any comments?  I want to avoid Raney Nickel as it is pyrrophoric!
 
 
 
 
    Rhodium
(Chief Bee)
12-15-03 10:58
No 477027
      And Lithium isn't?     

And Lithium isn't?

The Hive - Clandestine Chemists Without Borders
 
 
 
 
    roger2003
(Hive Bee)
12-15-03 16:38
No 477104
      Dimethoxytetrahydrofuran     

If you read this JACS -Article, I think, you know more

Post 458701 (Rhodium: "2,5-Dimethoxy-tetrahydrofuran from Furan", Methods Discourse)

roger2003
 
 
 
 
    tropine
(Newbee)
12-16-03 06:50
No 477178
      The JACS article is about RAney Nickel again     

thanks for the link, but the JACS article just talks about Raney Nickel again.  Yes Lithium is pyrrophoric, but I thought that Li in liquid ammonia is much less dangerous than Raney Nickel in H2, do you have any experience with Raney Nickel?
 
 
 
 
    Rhodium
(Chief Bee)
12-16-03 07:05
No 477182
      the pressure is the most dangerous part     

I thought that Li in liquid ammonia is much less dangerous than Raney Nickel in H2

I would say the other way around, as long as you have equipment which can take the necessary pressure.

The Hive - Clandestine Chemists Without Borders
 
 
 
 
    tropine
(Newbee)
12-16-03 08:58
No 477192
      2000 psi is not an option for any sane bee     

those pressures are just too high for my comfort zone.  The Li in ammonia is well documented on your site rhod, for the reduction of ephedrine.  Mr. Clean's writeup it pretty good, and all precautions are noted.  Chemically however do you think that the reduction will work on the dimethoxydihydrofuran C=C double bond? I am quite sure it will...no pressure and flammable gas, looks like a safer approach to me!
 
 
 
 
    roger2003
(Hive Bee)
12-16-03 11:12
No 477212
      dimethoxytetrahydrofuran     

If you carry out the reduction (or the workup) in aqueous solutions the dimethoxy converts to dihydroxy.

I read this a lot of years ago and cannot find again now.

Ca you send me the JACS article ?

.