19150-21-1

Usage

Synthesis Reference(s)

Tetrahedron Letters, 19, p. 191, 1978 DOI: 10.1016/S0040-4039(01)85081-4

InChI:InChI=1/C10H20/c1-3-5-7-9-10-8-6-4-2/h5,7H,3-4,6,8-10H2,1-2H3/b7-5+

Upstream product

• 2983-24-6 1,2-dibromo-1-ethoxybutane 
• 3761-92-0 n-hexylmagnesium bromide 
• 74-85-1 ethene 
• 629-05-0 n-octyne 
• 65949-99-7 Toluene-4-sulfonic acid 1-propyl-heptyl ester 
• 872-05-9 1-Decene 
• 91948-34-4 2-Methoxy-dec-3-yne 
• 111-66-0 oct-1-ene 
• 112-37-8 undecylenic acid 
• 546-67-8 lead(IV) tetraacetate 
• 71-43-2 benzene 
• 2384-85-2 3-decyne 
• 70859-25-5 (3R*,4R*)-decane-3,4-diol 
• 109-67-1 1-penten 

Downstream Products

• 53248-88-7 3,4-epoxydecane 
• 75-07-0 acetaldehyde 
• 123-72-8 butyraldehyde 
• 123-73-9 crotonaldehyde 

Relevant academic research and scientific papers

Organic Synthesis with Sulfones n0XXIX Stereospecific hydrogenolysis of vinylic sulfones with grignards and transition metal catalysts (1).

Hydrogenolysis of various vinylic sulfones to the corresponding olefins can be carried out by alkyl Grignard reagents with nickel or palladium catalysts.Yields are good to excellent.Retention of configuration is observed.The influence of ligands is discussed.

Extension of surface organometallic chemistry to metal?organic frameworks: Development of a well-defined single site [(≡Zr? O?)W(=O)(CH2TBu)3] olefin metathesis catalyst

We report here the first step by step anchoring of a W(≡CtBu)(CH2tBu)3 complex on a highly crystalline and mesoporous MOF, namely Zr-NU-1000, using a Surface Organometallic Chemistry (SOMC) concept and methodology. SOMC allowed us to selectively graft the complex on the Zr6 clusters and characterize the obtained single site material using state of the art experimental methods including extensive solid-state NMR techniques and HAADF-STEM imaging. Further FT?IR spectroscopy revealed the presence of a W=O moiety arising from the in situ reaction of the W≡CtBu functionality with the coordinated water coming from the 8-connected hexanuclear Zr6 clusters. All the steps leading to the final grafted molecular complex have been identified by DFT. The obtained material was tested for gas phase and liquid phase olefin metathesis and exhibited higher catalytic activity than the corresponding catalysts synthesized by different grafting methods. This contribution establishes the importance of applying SOMC to MOF chemistry to get well-defined single site catalyst on MOF inorganic secondary building units, in particular the in situ synthesis of W=O alkyl complexes from their W carbyne analogues.

Anti-Markovnikov Hydroheteroarylation of Unactivated Alkenes with Indoles, Pyrroles, Benzofurans, and Furans Catalyzed by a Nickel-N-Heterocyclic Carbene System

We report the catalytic addition of C-H bonds at the C2 position of heteroarenes, including pyrroles, indoles, benzofurans, and furans, to unactivated terminal and internal alkenes. The reaction is catalyzed by a combination of Ni(COD)2 and a sterically hindered, electron-rich N-heterocyclic carbene ligand or its analogous Ni(NHC)(arene) complex. The reaction is highly selective for anti-Markovnikov addition to α-olefins, as well as for the formation of linear alkylheteroarenes from internal alkenes. The reaction occurs with substrates containing ketones, esters, amides, boronate esters, silyl ethers, sulfonamides, acetals, and free amines.

General catalyst control of the monoisomerization of 1-alkenes to trans -2-alkenes

After searching for the proper catalyst, the dual challenges of controlling the position of the double bond, and cis/trans-selectivity in isomerization of terminal alkenes to their 2-isomers are finally met in a general sense by mixtures of (C5Me5)Ru complexes 1 and 3 featuring a bifunctional phosphine. Typically, catalyst loadings of 1 mol % of 1 and 3 can be employed for the production of (E)-2-alkenes at 40-70 C. Catalyst comprising 1 and 3 avoids more than any other known example the thermodynamic equilibration of alkene isomers, as the trans-2-alkenes of both nonfunctionalized and functionalized alkenes are generated.

Stabilization of long-chain intermediates in solution. octyl radicals and cations

The rearrangements of 1-octyl, 1-decyl and 1-tridecyl intermediates obtained from thermal lead(IV) acetate (LTA) decarboxylation of nonanoic, undecanoic and tetradecanoic acid were investigated experimentally through analysis and distribution of the products. The relationships between 1,5-, 1,6- and possibly existing 1,7-homolytic hydrogen transfer in 1-octyl-radical, as well as successive 1,2-hydride shift in corresponding cation have been computed via Monte-Carlo method. Taking into account that ratios of 1,5-/1,6-homolytic rearrangements in 1-octyl- and 1-tridecyl radical are approximately the same, the simulation shows very low involvement of 1,7-hydrogen rearrangement (1,5-/1,6-/1,7-hydrogen rearrangement = 85:31:1) in 1-octyl radical.

A selective Ru-catalyzed semireduction of alkynes to Z olefins under transfer-hydrogenation conditions

By using a readily available, air- and moisture-stable dihydrido-Ru complex, a variety of Z olefins are accessible under transfer-hydrogenation conditions with formic acid as the hydrogen source in excellent yields and Z/E selectivities. A discerning transformation: Z-Configured C=C bonds are stereoselectively formed from alkynes in the presence of a Ru catalyst with formic acid as the sole H2 source at room temperature (see scheme). A variety of functional groups are compatible with this novel procedure. Operational simplicity and the lack of overreduction products are characteristics for this unprecedented process.

Rhenium-catalyzed didehydroxylation of vicinal diols to alkenes using a simple alcohol as a reducing agent

A new method for the catalytic didehydroxylation of vicinal diols is described. Employing a readily available low-valent rhenium carbonyl complex and a simple alcohol as a reducing agent, both terminal and internal vicinal diols are deoxygenated to olefins in good yield. The optional addition of acid (TsOH, H2SO4) provides access to lower reaction temperatures. This new system enables the transformation of a four-carbon sugar polyol into an oxygen-reduced compound, providing promising evidence for its practical application to produce unsaturated compounds from biomass-derived materials.

An efficient didehydroxylation method for the biomass-derived polyols glycerol and erythritol. Mechanistic studies of a formic acid-mediated deoxygenation

An efficient 1,2-deoxygenation method, involving an unexpected mechanism, was found for simple diols and for biomass-derived polyols (glycerol and erythritol) that results in the conversion of the 1,2-dihydroxy group to a carbon-carbon double bond.

TRANSITION METAL COMPLEXES

A transition metal complex which is a bis-arylimine pyridine MXn complex, comprising a bis-arylimine pyridine ligand having the formula (I), wherein R1-R5, R7-R9, R12 and R14 are each, independently, hydrogen, optionally substituted hydrocarbyl, an inert functional group, or any two of R1-R3 and R7-R9 vicinal to one another taken together may form a ring, and R6 is hydrogen, optionally substituted hydrocarbyl, an inert functional group, or taken together with R7 or R4 to form a ring, R10 is hydrogen, optionally substituted hydrocarbyl, an inert functional group, or taken together with R9 or R4 to form a ring, R11 is hydrogen, optionally substituted hydrocarbyl, an inert functional group, or taken together with R12 or R5 to form a ring, R15 is hydrogen, optionally substituted hydrocarbyl, an inert functional group, or taken together with R14 or R5 to form a ring, provided that R13 and at least one of R12 and R14 are independently selected from optionally substituted C1-C30 alkyl, optionally substituted C4-C30 alkyloxy, halogen and optionally substituted C5-C20 aryl, or R13 taken together with R12 or R14 form a ring, or R12 taken together with R11 form a ring and R14 taken together with R15 form a ring, and provided that at least one of R12, R13 and R14 is optionally substituted C4-C30 alkyloxy; M is a transition metal atom in particular selected from Ti, V, Cr, Mn, Fe, Co, Ni, Pd, Rh, Ru, Mo, Nb, Zr, Hf, Ta, W, Re, Os, Ir or Pt; n matches the formal oxidation state of the transition metal atom M; and X is halide, optionally substituted hydrocarbyl, alkoxide, amide, or hydride. The transition metal complexes of the present invention, their complexes with non-coordinating anions and catalyst systems containing such complexes have good solubility in non-polar media and chemically inert non--polar solvents especially aromatic hydrocarbon solvents. The catalyst systems can be used for a wide range of (co-)oligomerization, polymerization and dimerization reactions.

METHOD FOR ISOMERIZING ORGANIC COMPOUND

PROBLEM TO BE SOLVED: To provide a method for isomerizing a compound bearing a hydrocarbon group having a carbon-carbon double bond which permits transfer of the carbon-carbon double bond of the compound without using a catalyst or an organic solvent. SOLUTION: The method for isomerizing the compound comprises transferring the position of the carbon-carbon double bond by causing the compound bearing the hydrocarbon group having the carbon-carbon double bond to non-catalytically react in a reaction medium in a high-temperature and high-pressure state. Thus, the isomer having the double bond transferred is obtained in a short time in one step by pressing the compound bearing the hydrocarbon group having the carbon-carbon double bond into high-temperature high-pressure water as a reaction site at a high speed. Neither waste nor wastewater to dispose of is discharged from the manufacturing processes.