Reactions of organolithium compounds and Grignard reagents with lithium carboxylates

1975 ◽  
Vol 40 (12) ◽  
pp. 1770-1773 ◽  
Author(s):  
Robert Levine ◽  
Marvin J. Karten ◽  
William M. Kadunce
Keyword(s):  
Grignard Reagents ◽  
Organolithium Compounds

PREPARATION OF C14-LABELLED ACIDS FROM C14O2 AND ARYL LITHIUM COMPOUNDS

1959 ◽  
Vol 37 (12) ◽  
pp. 1439-1446 ◽  
Author(s):  
A. C. Neish
Keyword(s):  
Benzoic Acid ◽  
Barium Carbonate ◽  
Grignard Reagents ◽  
Similar Sequence ◽  
Butyl Lithium ◽  
Organolithium Compounds ◽  
Lithium Compounds

A simplified technique was developed for carbonation of Grignard reagents or organolithium compounds, with C14O2 generated from barium carbonate. 3,4-(Dibenzyloxy)-bromobenzene was treated with n-butyl lithium in ether and then with C14O2 to give 3,4-(dibenzyloxy)-benzoic acid-carboxyl-C14. The yield was 74% based on barium carbonate. 2,6-Dichlorobenzoic acid-carboxyl-C14 (yield 77%) and 3,5-dichlorobenzoic acid-carboxyl-C14 (yield 76%) were prepared from the corresponding dichlorobromobenzenes by a similar sequence of reactions. Attempts to synthesize 2,4- and 2,5-dichlorobenzoic acids by this route gave poor yields of unidentified acids, from which the expected products could not be isolated.

STRUCTURE OF GRIGNARD REAGENTS AND ORGANOLITHIUM COMPOUNDS

1963 ◽  
pp. 767-773 ◽  
Author(s):  
Gideon Fraenkel ◽  
David G. Adams ◽  
James Williams
Keyword(s):  
Grignard Reagents ◽  
Organolithium Compounds

PREPARATION OF C14-LABELLED ACIDS FROM C14O2 AND ARYL LITHIUM COMPOUNDS

1959 ◽  
Vol 37 (1) ◽  
pp. 1439-1446
Author(s):  
A. C. Neish
Keyword(s):  
Benzoic Acid ◽  
Barium Carbonate ◽  
Grignard Reagents ◽  
Similar Sequence ◽  
Butyl Lithium ◽  
Organolithium Compounds ◽  
Lithium Compounds

A simplified technique was developed for carbonation of Grignard reagents or organolithium compounds, with C14O2 generated from barium carbonate. 3,4-(Dibenzyloxy)-bromobenzene was treated with n-butyl lithium in ether and then with C14O2 to give 3,4-(dibenzyloxy)-benzoic acid-carboxyl-C14. The yield was 74% based on barium carbonate. 2,6-Dichlorobenzoic acid-carboxyl-C14 (yield 77%) and 3,5-dichlorobenzoic acid-carboxyl-C14 (yield 76%) were prepared from the corresponding dichlorobromobenzenes by a similar sequence of reactions. Attempts to synthesize 2,4- and 2,5-dichlorobenzoic acids by this route gave poor yields of unidentified acids, from which the expected products could not be isolated.

Sign in / Sign up

Export Citation Format

Share Document