76524-56-6

Upstream product

• 35998-93-7 tri-n-butylcrotyltin 
• 4392-24-9 Cinnamyl bromide 
• 21040-45-9 Cinnamyl acetate 
• 38169-04-9 (E)-crotyl iodide 
• 21087-29-6 trans-3-phenylprop-2-enyl chloride 
• 100-42-5 styrene 
• 78-79-5 isoprene 
• 18292-28-9 1-(trimethylsilyl)but-2-ene 
• 40595-34-4 (E)-trimethyl(3-phenylallyl)silane 
• 934-10-1 3-phenylbut-1-ene 
• 111195-58-5 but-2-enylzinc bromide 
• 114067-35-5 ((E)-2-butenyl)trifluorosilane 
• 563-52-0 2-chloro-3-butene 
• 54962-99-1 cinnamyllithium 

Relevant academic research and scientific papers

Diene compound and process for producing the same

The invention provides a chain diene compound with desirable regioselectivity, in the presence of a specific ruthenium compound. This chain diene compound is a promising raw material for terpene. It has a structure represented by the general formula (IX): wherein R1represents H, a C1-C6alkyl group which may be substituted or a C2-C6alkenyl group which may be substituted, R2represents a phenyl group which may have a C1-C4alkyl group or a C1-C12acyloxy group which may have a phenyl group or a naphthyl group, or a benzyl group or R2is a hydroxy group which reversibly forms an aldehyde group through shifting of the position of the double bond adjacent to said hydroxy group. The chain diene compound is produced by reacting 2-substituted-1,3-butadienes with terminal olefins in the presence of a ruthenium compound in a hydrophilic solvent. Further, the above method provides an inexpensive process for preparing a mild fragrant component and a perfume composition, such as 4-methyl-5-hexen-1-al and 4-vinyl-8-methyl-7-nonenal.

Selective Alkylation and Allylation of Allylic Halides by Tetraorganoidates: Regio- and Stereo-selective Synthesis of Rosefuran and Sesquirosefuran

Tetraalkylindanes regioselectively alkylate allylic bromides at the α-carbon.In this way, 1,5-dienes have been regio- and stereo-selectively synthesized by the allyl-allyl coupling of allylic bromides and allylic indates, including rosefuran 1 and sequirosefuran 3.

Oxovanadium-induced oxidative desilylation of allylic and benzylic silanes

Cinnamyltrimethylsilane underwent desilylation via one-electron oxidation with VO(OEt)Cl2, which was applied to the cross-coupling with the less oxidizable allylic silanes to give the corresponding 1,5-hexadienes. Chlorination or aromatization

Application of Indium Ate Complexes to Synthetic Chemistry. Selective Conjugate Addition to Enones and Coupling with Allylic Halides

Tetraorganoindium ate complexes, prepared by the addition of organolithium reagents to trialkylindium, reacted with α,β-unsaturated ketones in a 1,4-addition fashion; allylic indates derived from allylic indium sesquihalides coupled with allylic halides regio- and stereo-specifically to give high yields of hed-to-tail 1,5-dienes.

COPPER- AND NICKEL-CATALYSIS IN SN2'- AND SN2-REGIOSELECTIVE ALLYLATION OF ORGANOZINC REAGENTS

Allylation of organozinc reagents in the presence of a copper catalyst takes place in a highly SN2'-selective manner, whereas that in the presence of a nickel catalyst occurs with excellent SN2-selectivity.

Regioselective Head-to-tail Coupling of Allylic Trialkylstannanes with Allylic Halides under High Pressure

Allylic trialkylstannanes (1) regioselectively react with allylic halides (2) at room temperature under high pressure (10 kbar) to give head-to-tail coupling products (3) in high yields.

Reaction Of Allylic Boron and Aluminium "Ate" Complexes with Organic Halides and Carbonyl Compounds. Trialkylboranes as Regio-, Stereo-, and Chemoselective Control Elements

Lithium allylic boron ate complexes, prepared by the addition of trilakylboranes to an ether solution of allylic lithium compounds, regioselectively react with allylic halides to produce head-to-tail 1,5-dienes (eq 1).The ate complexes are also prepared from the reaction of allylic boranes with alkyllithium derivatives.Magnesium or copper allylic boron ate complexes are less effective.Lithium crotyl boron ate complexes undergo a rapid reaction with aldehydes with good threoselectivity (eq 2).The selectivity is affected by the steric hindrance of trialkylboranes, as explained by the steric parameters of the 6-membered transition state.The ate complexes react with α,β-unsaturated ketones in a competitive manner of 1,2 and 1,4 addition, while they add to cinnamaldehyde exclusively in a 1,2 manner.The chemoselective aspects are only investigated. 1H and 13 C NMR spectra of lithium allylic boron ate complexes clearly indicate (i) the prevention of allylic rearrangement, (ii) the predominant trans geometry of the crotyl unit in comparison with the corresponding trivalent crotylboron, and (iii) the relative importance of ?-? conjugation between the double bond and the carbon-boron bond (eq 3).

ALLYLSTANNANES AS ELECTROFUGAL PARTNERS IN ALLYLIC ALKYLATION

Unsymmetrical allyl-allyl couplings occur between allylstannanes and allyl acetates catalyzed by palladium(0) and a novel direct coupling of an allyl acetate in the presence of a distannane and a palladium(0) catalyst is also possible.