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All 2 posts Subject: New route to Phenyl-2-propanone Please login to post Down

Rhodium
(Chief Bee)
01-19-02 13:32
No 258307
User Picture       New route to Phenyl-2-propanone

A new route to P2P, starting with bromobenzene

[Bull Soc Chem Jap 57, 242 (1984)]

To a stirred solution of an aryl bromide (60 mmol), isopropenyl acetate (9g, 90 mmol) and dichlorobis(tri-o-tolylphosphine)palladium (0.47g, 0.67 mmol) in dry toluene (30 ml), under nitrogen, was added tributyltin methoxide (25.9 ml, 90 mmol; Aldrich). The mixture was stirred and heated at 100 deg C for 5 hr, cooled and the solvent evaporated in vacuo. The residue was chromatographed on silica gel, to afford the aryl-2-propanone in 67% yield.

Rhodium
(Chief Bee)
10-06-04 03:06
No 534619
User Picture       P2P by Pd-catalyzed arylation of acetone enolether
(Rated as: excellent)

Arylation and 1-Alkenylation on α-Position of Ketones via Tributyltin Enolates Catalyzed by Palladium Complex
Masanori Kosugi, Isao Hagiwara, Takao Sumiya. and Toshihiko Migita
Bull. Chem. Soc. Jpn. 57, 242-246 (1984) (https://www.rhodium.ws/pdf/arylation.isopropenylacetate.pd-busnome.pdf)

Abstract
The reaction of tributyltin enolates, prepared from tributyltin methoxide and enol acetates in situ, with aryl and 1-alkenyl bromides in the presence of dichlorobis(tri-o-tolylphosphine)palladium was found to give α-aryl and α-(1-alkenyl)ketones, respectively, in good yields with essentially complete retention of the enol acetate regiochemistry.

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	All 2 posts		Subject: New route to Phenyl-2-propanone		Please login to post		Down


		Rhodium (Chief Bee) 01-19-02 13:32 No 258307				New route to Phenyl-2-propanone
						A new route to P2P, starting with bromobenzene [Bull Soc Chem Jap 57, 242 (1984)] To a stirred solution of an aryl bromide (60 mmol), isopropenyl acetate (9g, 90 mmol) and dichlorobis(tri-o-tolylphosphine)palladium (0.47g, 0.67 mmol) in dry toluene (30 ml), under nitrogen, was added tributyltin methoxide (25.9 ml, 90 mmol; Aldrich). The mixture was stirred and heated at 100 deg C for 5 hr, cooled and the solvent evaporated in vacuo. The residue was chromatographed on silica gel, to afford the aryl-2-propanone in 67% yield.



		Rhodium (Chief Bee) 10-06-04 03:06 No 534619				P2P by Pd-catalyzed arylation of acetone enolether (Rated as: excellent)
						Arylation and 1-Alkenylation on α-Position of Ketones via Tributyltin Enolates Catalyzed by Palladium Complex Masanori Kosugi, Isao Hagiwara, Takao Sumiya. and Toshihiko Migita Bull. Chem. Soc. Jpn. 57, 242-246 (1984) (https://www.rhodium.ws/pdf/arylation.isopropenylacetate.pd-busnome.pdf) Abstract The reaction of tributyltin enolates, prepared from tributyltin methoxide and enol acetates in situ, with aryl and 1-alkenyl bromides in the presence of dichlorobis(tri-o-tolylphosphine)palladium was found to give α-aryl and α-(1-alkenyl)ketones, respectively, in good yields with essentially complete retention of the enol acetate regiochemistry. ^{The Hive - Clandestine Chemists Without Borders}

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