2787-45-3

Usage

InChI:InChI=1/C6H10/c1-4-6(3)5-2/h4-5H,1H2,2-3H3/b6-5-

Upstream product

• 918-85-4 3-hydroxy-3-methyl-1-pentene 
• 689-97-4 3-buten-1-yne 
• 4143-42-4 (Z)-azomethane 
• 123873-22-3 (E)-3-Methyl-5-trimethylsilanyl-pent-3-en-2-ol 
• 2747-52-6 3-methylenepentan-2-ol 
• 2206-26-0 [D₃]acetonitrile 
• 1115-08-8 3-methyl-1,4-pentadiene 

Downstream Products

• 91974-56-0 4,4,5,5-Tetracyan-2,3-dimethyl-cyclohexen 
• 104722-44-3 (1E,3Z)-1-(3-methylpenta-1,3-dienyl)benzene 
• 72623-07-5 threo-1-chloro-4-<(2-chloro-1,2-dimethyl-3-butenyl)thio>benzene 
• 72623-03-1 (Z)-1-chloro-4-<(2-chloro-3-methyl-3-pentenyl)thio>benzene 

Relevant academic research and scientific papers

A Series of Crystallographically Characterized Linear and Branched σ-Alkane Complexes of Rhodium: From Propane to 3-Methylpentane

Using solid-state molecular organometallic (SMOM) techniques, in particular solid/gas single-crystal to single-crystal reactivity, a series of σ-alkane complexes of the general formula [Rh(Cy2PCH2CH2PCy2)(ηn:ηm-alkane)][BArF4] have been prepared (alkane = propane, 2-methylbutane, hexane, 3-methylpentane; ArF = 3,5-(CF3)2C6H3). These new complexes have been characterized using single crystal X-ray diffraction, solid-state NMR spectroscopy and DFT computational techniques and present a variety of Rh(I)···H-C binding motifs at the metal coordination site: 1,2-η2:η2 (2-methylbutane), 1,3-η2:η2 (propane), 2,4-η2:η2 (hexane), and 1,4-η1:η2 (3-methylpentane). For the linear alkanes propane and hexane, some additional Rh(I)···H-C interactions with the geminal C-H bonds are also evident. The stability of these complexes with respect to alkane loss in the solid state varies with the identity of the alkane: from propane that decomposes rapidly at 295 K to 2-methylbutane that is stable and instead undergoes an acceptorless dehydrogenation to form a bound alkene complex. In each case the alkane sits in a binding pocket defined by the {Rh(Cy2PCH2CH2PCy2)}+ fragment and the surrounding array of [BArF4]- anions. For the propane complex, a small alkane binding energy, driven in part by a lack of stabilizing short contacts with the surrounding anions, correlates with the fleeting stability of this species. 2-Methylbutane forms more short contacts within the binding pocket, and as a result the complex is considerably more stable. However, the complex of the larger 3-methylpentane ligand shows lower stability. Empirically, there therefore appears to be an optimal fit between the size and shape of the alkane and overall stability. Such observations are related to guest/host interactions in solution supramolecular chemistry and the holistic role of 1°, 2°, and 3° environments in metalloenzymes.

Catalytic hydromagnesation of di- and polymethyl-substituted 1,3-butadienes

Hydromagnesation of di- and polymethyl-substituted 1,3-butadienes with alkylmagnesium halides in the presence of Ni(PPh3)2Cl2 and NiPy4Cl2 was studied.

STANNYLDIENES, NEW TOOLS FOR ORGANIC SYNTHESIS. PREPARATION AND REACTIVITY.

Tributylstannyl-1,3-dienes could be considered synthetic equivalents of conjugated dienic anions.The preparation of differently substituted 2- and 3-trialkylstannyl-1,3-dienes is reported starting from propargyltrimethylsilane.The position of the stannyl moiety on the dienic skeleton can be controlled by hydrostannylation of (trimethylsilyl)propargyl alcohols or stannyl cupration of (trimetylsilyl)propargyl ketones.The so obtained stannyldienes are submitted to Diels Alder reaction and the corresponding cycloadducts functionalized through the C-Sn bond.Stannyldienes are also suitable for a regiocontrolled transfer of the dienic structure by : a) tin-lithium exchange and further reaction with aldehydes to give conjugated dienic alcohols; b)coupling with acyl chlorides in the presence of palladium catalysts to give conjugated dienic ketones; c) AlCl3 promoted reaction with acyl chlorides to give allenic ketones.

Untersuchungen zur Kinetik und zum Mechanismus der Addition von Methylradikalen an Vinylacetylen

The addition of methyl radicals to vinylacetylen has been studied at 573 K.The methyl radicals were produced by thermolysis of azomethane.The attack occurs exclusively in the terminal positions and predominantly at the triple bond.The value of the rate constant amounts to k2.1 + k2.2 = 5.1E6 l mol-1s-1.The main steps and the formed types of radicals are deduced from the stable products.Without azomethane vinylacetylene is consumed by a slow conversion of second order.The activation parameters of this dimerisation were estimated at 553-593 K.