5732-02-5Relevant academic research and scientific papers
Direct Metallation of Isoprene
Klusener, Peter A. A.,Hommes, Hendrik H.,Verkruijsse, Hermenn D.,Brandsma, Lambert
, p. 1677 - 1678 (1985)
Treatment of isoprene with an excess of the couple potassium t-butoxide-lithium tetramethylpiperidine in tetrahydrofuran, followed by addition of a higher alkyl bromide or oxirane, gives the dienes H2C=CHC(=CH2)CH2R (R = alkyl or -CH2CH2OH) in reasonable yields.
Method for preparing neophytadiene compounds from fatty acid
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, (2017/08/29)
The invention relates to a method for preparing neophytadiene compounds from fatty acid. The method comprises the following steps: firstly preparing lipid-containing ketene from fatty acid in two ways, namely a way a comprising the steps of dehydrogenizing the fatty acid by a deprotonation reagent and then reacting with a vinyl Grignard reagent or vinyl lithium to generate ketene compounds, and a way b comprising steps of activating the fatty acid by carbodiimide reagents, then reacting with dialkyl hydroxylamine or hydrochloride thereof to generate N-alkoxy amide compounds (Weinreb amides) and then reacting with the vinyl Grignard reagent or vinyl lithium to generate the ketene compounds; and finally carrying out reaction on the ketene compounds and an olefination reaction reagent to generate the neophytadiene compounds.
Expanding the scope of biomass-derived chemicals through tandem reactions based on oxorhenium-catalyzed deoxydehydration
Shiramizu, Mika,Toste, F. Dean
, p. 12905 - 12909 (2014/01/06)
New modes of DODH: Oxorhenium compounds act as deoxydehydration(DODH)/acid dual-purpose catalysts to transform biomass-derived diol substrates into a variety of commodity chemical precursors. The power of this approach is highlighted by a tandem [1,3]-OH shift/DODH of 2-ene-1,4-diols and 2,4-diene-1,6-diols, and by a DODH/esterification sequence of sugar acids to unsaturated esters for the production of polymers and plasticizers. Copyright
Efficient preparation of terminal conjugated dienes by coupling of dienol phosphates with grignard reagents under iron catalysis
Cahiez, Gerard,Habiak, Vanessa,Gager, Olivier
supporting information; experimental part, p. 2389 - 2392 (2009/05/27)
(Chemical Equation Presented) An efficient new route to prepare stereoselectively terminal conjugated dienes by coupling Grignard reagents and dienol phosphates in the presence of Fe(acac)3 is described. The synthetic utility of this new iron-catalyzed procedure is illustrated by the synthesis of the pheromone of Diparopsis castanea according to a very expeditious strategy.
ON THE DIRECT METALATION OF ISOPRENE
Klusener, P. A. A.,Tip, L.,Brandsma, L.
, p. 2041 - 2064 (2007/10/02)
Isoprene has been metalated in tetrahydrofuran with an excess of sterically hindered potassium dialkylamides, prepared by combining equimolar amounts of the corresponding lithium amide and potassium tert-butoxide.Subsequent reaction with oxirane, alkyl bromides, and pivaldehyde gave the expected coupling products in reasonable yields.Coupling with (CH3)2CHCH2CH=O and (CH3)2C=CHCH=O afforded the bark beetle pheromones (+/-)-ipsenol and (+/-)-ipsdienol in low yields.
REACTIONS OF ORGANOCOPPER REAGENTS DERIVED FROM CHLOROPRENE. CONJUGATE ADDITION AND NUCLEOPHILIC SUBSTITUTION
Shea, K. J.,Pham, P. Q.
, p. 1003 - 1006 (2007/10/02)
Organocopper reagents derived from 2-(1,3-butadienyl) magnesium chloride react regiospecifically with a α,β-unsaturated carbonyl compounds to give 1,4-addition products of 2-substituted-1,3-butadienes.
ALLENES AND ACETYLENES XXVI. ORGANOCUPRATE REACTIONS OF 1,3-ALKADIEN-2-YL PHOSPHATES. A NEW APPROACH TO THE SYNTHESIS OF ALLENES
Claesson, Alf,Quader, Abdul,Sahlberg, Christer
, p. 1297 - 1300 (2007/10/02)
Allenic hydrocarbons and one Γ-allenic ketone were prepared in poorto good yields by the reactions of diethyl 1-methylene-2-propenyl phosphate and diethyl 1-(1-cyclohexenyl)vinyl phosphate with various organocuprates.
SYNTHESIS OF CONJUGATED DIENES BY NICKEL-CATALYZED REACTIONS OF 1,3-ALKADIEN-2-YL PHOSPHATES WITH GRIGNARD REAGENTS
Sahlberg, Christer,Quader, Abdul,Claesson, Alf
, p. 5137 - 5138 (2007/10/02)
2-Substitued 1,3-alkadienes were prepared in good yields by reactions of diethyl 1-methyl-2-propenyl phosphate and diethyl 1-methylene-3-phenyl-2-propenyl phosphate with various Grognard reagents in the presence of nickel(II) catalysts.
