Blaise ketone synthesis

The Blaise ketone synthesis is a name reaction in organic chemistry . It was published in 1907 by Edmond Blaise (1872-1939).

Overview reaction

In the Blaise ketone synthesis, an organozinc halogen compound reacts with an acyl halide to form a ketone .

Reaction mechanism

In the proposed reaction mechanism, the organozinc chloride compound reacts directly with the acyl halide. After splitting off zinc chloride, the desired ketone is formed:

The yield of the ketone in this reaction can be greater than 80%.

modification

The Blaise ketone synthesis has been expanded to synthesize α, β-unsaturated ketones. The reaction is the Blaise-Maire reaction. In addition, the organozinc chloride compound was replaced with an organocadmium reagent in order to increase the yield.

application

The Blaise ketone synthesis is important in organic synthesis.

Individual evidence

↑ ^a ^b ^c ^d ^e 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 ^c ^d ^e R. K. Summerbell, LN Bauer: Studies in the Dioxane Series. III. The Use of Zinc and Cadmium Chlorides in the Grignard Synthesis of Alkyl Substituted Dioxanes . In: Journal of the American Chemical Society . tape 58 , no. 5 , May 1, 1936, p. 759-761 , doi : 10.1021 / ja01296a019 .
↑ NI Sheverdina, IE Paleeva, LV Abramova, VS Yakovleva, LA Kocheshkov: Organozinc compounds of the RZnX class . In: Bulletin of the Academy of Sciences of the USSR, Division of chemical science . tape 16 , no. 5 , May 1, 1967, pp. 1038-1042 , doi : 10.1007 / BF01176030 .

[: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] A ^b ^c ^d ^e R. K. Summerbell, LN Bauer: Studies in the Dioxane Series. III. The Use of Zinc and Cadmium Chlorides in the Grignard Synthesis of Alkyl Substituted Dioxanes . In: Journal of the American Chemical Society . tape 58 , no. 5 , May 1, 1936, p. 759-761 , doi : 10.1021 / ja01296a019 .

[3] NI Sheverdina, IE Paleeva, LV Abramova, VS Yakovleva, LA Kocheshkov: Organozinc compounds of the RZnX class . In: Bulletin of the Academy of Sciences of the USSR, Division of chemical science . tape 16 , no. 5 , May 1, 1967, pp. 1038-1042 , doi : 10.1007 / BF01176030 .