Methylenate Ester carbonyl?

Thread View: sci.chem.organomet

3 messages

[T] Back to Threads [V] Tree View [G] Group Articles

3 total messages Started by Greg Cook|xxxxxx Thu, 31 Dec 1992 14:29

Author: Greg Cook|xxxxxx
Date: Thu, 31 Dec 1992 14:29

16 lines
1118 bytes

I think I saw somewhere an organometallic reagent that will methylenate the
carbonyl of an ester but I don't remember what it is.  Does Tebbe's reagent
do this or is it limited to aldehydes and ketones?  What reagent does?

      R - C - OMe     ------->     R - C - OMe
          ||             ?             ||
          O                            CH2

Does it work for amide carbonyls as well?

Thanks for your help!

     Gregory R. Cook         |  INTERNET:    gcook@horus.cem.msu.edu
 Department of Chemistry     |               cookgreg@student.msu.edu
Michigan State University    |  BITNET:      cook@msucem.BITNET
 East Lansing, MI  48824     |  COMPUSERVE:  74170,3010

Re: Methylenate Ester carbonyl?

Author: Nathan Otto Siemers
Date: Fri, 01 Jan 1993 10:02

25 lines
1452 bytes

>>>>> On 31 Dec 92 14:29:03 GMT, gcook@horus.cem.msu.EDU (Greg
 Greg> Cook|xxxxxx) said: NNTP-Posting-Host: horus.cem.msu.edu

 Greg> I think I saw somewhere an organometallic reagent that will
 Greg> methylenate the carbonyl of an ester but I don't remember what
 Greg> it is.  Does Tebbe's reagent do this or is it limited to
 Greg> aldehydes and ketones?  What reagent does?

 Greg> R - C - OMe -------> R - C - OMe || ?  || O CH2

 Greg> Does it work for amide carbonyls as well?


	Tebbe's works for esters.  Don't know about amides.

	There is a  witch's brew call the Lombardo reagent that does
similar chemistry.  Actually discovered by a Japanese guy who got
jilted by history (I don't even remember his name!  :( )


	Nathan Siemers

--
--
/  | / /__|  /  /---/ /__| /  | /    nathan@chemres.tn.cornell.edu

Re: Methylenate Ester carbonyl?

#16

Author: Alan S Florjancic
Date: Fri, 08 Jan 1993 00:41

9 lines
1011 bytes

The latest edition of The Journal of Organic Chemistry(actually it is an 
Aldrich ad on the back cover) shows three different methods of forming a 
methylene from a carbonyl, including the Tebbe.  Of the three, which I do not 
recall from memory, the Tebbe seems to be the only one to work with esters.  I 
am sure the leading references they give in the ad should provide you with your
answers....

Alan S. Florjancic
The Ohio State University

Thread Navigation

This is a paginated view of messages in the thread with full content displayed inline.

Messages are displayed in chronological order, with the original post highlighted in green.

Use pagination controls to navigate through all messages in large threads.

Back to All Threads