Bourguel alkyne synthesis

The Bourguel alkyne synthesis is a name reaction in organic chemistry that was published in 1925 by M. Bourguel. With the synthesis, alkynes can be produced from 2,3-dibromo-1-propene.

Overview reaction

The Bourguel alkyne synthesis takes place in two reaction steps. First there is a reaction with a Grignard compound , followed by a reaction with sodium amide .

Reaction mechanism

In the proposed reaction mechanism, the 2,3-dibromo-1-propene first reacts in a Grignard reaction to synthesize a substituted 2-bromo-1-propene. A reaction with sodium amide follows to synthesize the desired alkyne.

The advantages of using sodium amide are the high yield and the possibility that internal alkynes can isomerize to terminal alkynes.

application

The Bourguel alkyne synthesis is used in the production of alkynes.

Individual evidence

↑ ^a ^b ^c ^d Zerong Wang: Comprehensive Organic Name Reactions and Reagents . John Wiley & Sons, Inc., Hoboken, NJ, USA 2010, ISBN 978-0-470-63885-9 , doi : 10.1002 / 9780470638859 .
↑ ^a ^b R. Lespieau, M. Bourguel: 2,3-Dibromopropene: Propene, 2,3-dibromo- . In: Organic Syntheses . John Wiley & Sons, Inc., Hoboken, NJ, USA 2003, ISBN 0-471-26422-9 , pp. 49-49 , doi : 10.1002 / 0471264180.os005.17 .
^ John R. Johnson, WL McEwen, THE IDENTIFICATION OF MONOSUBSTITUTED ACETYLENES. DERIVATIVES OF DIETHINYL MERCURY . In: Journal of the American Chemical Society . tape 48 , no. 2 , 1926, p. 469-476 , doi : 10.1021 / ja01413a025 .
^ Arthur J. Hill, Floyd Tyson, STUDIES ON THE PREPARATION OF THE HIGHER ACETYLENES. I. (PRELIMINARY PAPER.) DEHALOGENATION OF 1,1-DICHLOROHEPTANE IN THE VAPOR PHASE . In: Journal of the American Chemical Society . tape 50 , no. 1 , 1928, pp. 172–177 , doi : 10.1021 / ja01388a024 .

[:0-1] Zerong Wang: Comprehensive Organic Name Reactions and Reagents . John Wiley & Sons, Inc., Hoboken, NJ, USA 2010, ISBN 978-0-470-63885-9 , doi : 10.1002 / 9780470638859 .

[:1-2] R. Lespieau, M. Bourguel: 2,3-Dibromopropene: Propene, 2,3-dibromo- . In: Organic Syntheses . John Wiley & Sons, Inc., Hoboken, NJ, USA 2003, ISBN 0-471-26422-9 , pp. 49-49 , doi : 10.1002 / 0471264180.os005.17 .

[3] John R. Johnson, WL McEwen, THE IDENTIFICATION OF MONOSUBSTITUTED ACETYLENES. DERIVATIVES OF DIETHINYL MERCURY . In: Journal of the American Chemical Society . tape 48 , no. 2 , 1926, p. 469-476 , doi : 10.1021 / ja01413a025 .

[4] Arthur J. Hill, Floyd Tyson, STUDIES ON THE PREPARATION OF THE HIGHER ACETYLENES. I. (PRELIMINARY PAPER.) DEHALOGENATION OF 1,1-DICHLOROHEPTANE IN THE VAPOR PHASE . In: Journal of the American Chemical Society . tape 50 , no. 1 , 1928, pp. 172–177 , doi : 10.1021 / ja01388a024 .