41446-62-2

Upstream product

• 111-83-1 1-bromo-octane 
• 13154-13-7 (E)-1-bromohex-1-ene 
• 50965-96-3 (E)-1-methoxy-2-heptene 
• 42092-01-3 n-heptylmagnesium chloride 
• 629-27-6 1-Iodooctane 
• 693-02-7 hex-1-yne 
• 124-19-6 nonan-1-al 
• 29541-98-8 pentylidenetriphenylphosphorane 
• 1119-64-8 1-bromohexyne 
• 111-66-0 oct-1-ene 
• 17049-49-9 octylmagnesium bromide 
• 67532-02-9 ((Z)-1-Bromo-hex-1-enyl)-bis-(1,2-dimethyl-propyl)-borane 
• 67993-59-3 (1-iodo-1-hexenyl)bis(1,2-dimethylpropyl)borane 
• 67532-01-8 1-bromo-1-hexenyldicyclohexylborane 

Downstream Products

• 7433-78-5 cis-5-decene 
• 7206-25-9 trans-9-octadecene 
• 1779-13-1 octadeca-9Z-ene 
• 5557-31-3 9-octadecene 
• 7433-56-9 (E)-5-decene 

Relevant academic research and scientific papers

Tandem application of C-C bond-forming reactions with reductive ozonolysis

Several variants of reductive ozonolysis, defined here as the in situ generation of aldehydes or ketones during ozonolytic cleavage of alkenes, are demonstrated to work effectively in tandem with a number of C-C bond-forming reactions. For reactions involving basic nucleophiles (1,2- addition of Grignard reagents, Wittig or Horner-Emmons olefinations, and directed aldol reactions of lithium enolates), the one-pot process offers a rapid and high-yielding alternative to traditional two-step protocols.

Iron thiolate complexes: Efficient catalysts for coupling alkenyl halides with alkyl grignard reagents

Ironing out the kinks: Efficient new catalytic systems based on iron thiolates are described for the iron-catalyzed cross-coupling of alkyl Grignard reagents with alkenyl halides (see scheme). The reaction is highly chemo- and stereoselective. With this new procedure, the use of N-methylpyrrolidone as a co-solvent is no longer required. Copyright

Reaction of trialkyl(dibromomethyl)silanes or 1,2-bis(dibromomethyl)benzene with triorganomanganates. A facile and selective synthesis of alkenylsilanes and 1,2-diaryl-1,2-dihydrobenzocyclobutenes

Treatment of trialkyl(dibromomethyl)silanes with trialkylmanganates, derived from manganese(II) chloride and three molar amounts of Grignard reagents or alkyllithiums, provided (E)-1-trialkylsilyl-1-alkenes with high stereoselectivity in good yields. The reaction of trialkyl(dibromomethyl)silanes with alkylmagnesium halides proceeded in the presence of a catalytic amount of manganese(II) chloride. Treatment of 1,2-bis(dibromomethyl)benzene with triphenylmanganate gave 1,2-diphenyl-1,2-dihydrobenzocyclobutene.

Cobalt-catalyzed alkenylation of zinc organometallics

Organozinc halides and diorganozincs undergo cross-coupling reactions with either E- or Z-alkenyl iodides in the presence of catalytic amounts of Co(acac)2 or Co(acac)3 in THF:NMP at 55°C leading to polyfunctional alkenes with retent

Highly stereo and chemoselective iron-catalyzed alkenylation of organomagnesium compounds

In the presence of Fe(acac)3, Grignard reagents react readily with alkenyl halides (X = I, Br or Cl) in a THF/NMP mixture to give the cross-coupling products in high yields with an excellent stereoselectivity (≤99.5%). The scope of the reaction is very broad since a vast array of functional groups are tolerated (esters, nitriles, aromatic or aliphatic halides and even ketones). The procedure reported herein is an interesting alternative to the classical Pd- or Ni-catalyzed reactions, especially for preparative organic chemistry.

Manganese-catalyzed reaction of gem-dibrornoalkanes with Grignard reagents. Selective synthesis of alkenylsilanes

Treatment of dibromomethyltrialkylsilanes with butylmagnesium bromide in the presence of a catalytic amount of manganese(II) chloride provided (E)-1-trialkylsilyl-1-pentenes with high stereoselectivity in good yields.

Highly chemo- and stereoselective Fe-catalyzed alkenylation of organomanganese reagents

Organomanganese chlorides react with alkenyl iodides, bromides and chlorides in the presence of 3% Fe(acac)3. The reaction takes place under very mild conditions (THF-NMP, rt, 1h) to afford the substituted olefin in excellent yields with a high stereo- and chemoselectivity. Thus an unprotected keto alkenyl chloride selectively gives the corresponding keto olefin. From a preparative point of view, this procedure is the first real alternative to the Pd- and Ni-cross coupling reaction used until now.

SYNTHESIS OF PHEROMONES, IV. CHEMISTRY OF THE WITTIG REACTION, I. EFFECTS OF REACTION CONDITIONS ON THE STEREOSELECTIVITY AND YIELD OF THE WITTIG REACTION

The reactions of nonstabilized triphenylphosphorus ylides with aldehydes have been studied in detail.The stereochemistry and yields of the alkene products are highly dependent upon base used for the generation of the ylide, the solvent and reaction temperature.The synthesis of sex pheromone components by Wittig reaction are also described.

Vinylic Organoboranes. 6. A General Synthesis of (E)-Disubstituted Alkenes or Ketones via the (E)-(1-Substituted-1-alkenyl)boronic Esters

Development of a general stereospecific synthesis of (E)-disubstituted alkenes utilizing a variety of hydroborating agents such as monohaloborane, thexylborane, thexylchloroborane, and dibromoborane is discussed.Hydroboration of 1-halo-1-alkynes with dial

NOVEL SYNTHESIS OF INTERNAL ALKENYLDIALKYLBORANE BY THE REACTION OF 1-HALO-1-ALKENYLDIALKYLBORANE WITH GRIGNARD REAGENT.

To synthesize internal alkenyldialkylboranes, coupling reactions were carried out by using 1-halo-1-alkenyldialkylboranes and Grignard reagents. Hydrogen peroxide oxidation and protonolysis with acetic acid of the reaction product revealed that internal (E)-alkenyldialkylborane was formed in 60-90% yield.