57642-95-2

Upstream product

• 123-15-9 2-methylvaleraldehyde 
• 96-17-3 2-Methylbutyraldehyde 
• 107-18-6 allyl alcohol 

Downstream Products

• 123-38-6 propionaldehyde 
• 1394035-47-2 (2E)-but-2-en-1-yl 4-(trifluoromethyl)phenyl ether 

Relevant academic research and scientific papers

Infrared Spectra of Gas-Phase 1- and 2-Propenol Isomers

Fourier transform infrared spectra of isolated 1-propenol and 2-propenol in the gas-phase have been collected in the range of 900-3800 cm-1, and the absolute infrared absorption cross sections reported for the first time. Both cis and trans isomers of 1-propenol were observed with the trans isomer in greater abundance. Syn and anti conformers of both 1- and 2-propenol were also observed, with abundance consistent with thermal population. The FTIR spectrum of the smaller ethenol (vinyl alcohol) was used as a benchmark for our computational results. As a consequence, its spectrum has been partially reassigned resulting in the first report of the anti-ethenol conformer. Electronic structure calculations were used to support our experimental results and assign vibrational modes for the most abundant isomers, syn-trans-1-propenol and syn-2-propenol.

Generation of Simple Enols in Non-aqueous Solution by Fast Double-bond Migration of Allylic Alcohols with Rhodium(I) and Iridium(I) Complexes

The complexes ClO4 1 and ClO4 2 (cod = cycloocta-1,5-diene), rapidly catalyse the double-bond migration of 2-ethylprop-2-en-1-ol 3 and prop-2-en-1-ol 4, respectively to generate a significant amount of the enols 2-methylbut-1-en-1-ol 5 and prop-1-en-1-ol 6 in the absence of a solvent and in CD3COCD3.Both enols 5 and 6 are quite stable and slowly undergo ketonization to the corresponding carbonyl compounds at room temperature in the absence of a solvent and in aprotic solvents.Detailed 1H NMR spectral data at 300 MHz suggest that two isomers (Z and E) of the compound 5 are simultaneously produced in the reaction of 3 and 1, the ratio of the isomers (major : minor) being ca. 6-9:1.Reaction of compound 4 with 2 also generates the Z (major) and E isomers (minor) of 6.The Z isomer initially generated rapidly undergoes isomerization to give the E isomer in the presence of 2, while both the Z and E isomers relatively slowly undergo ketonization.Additional 1H and 13C NMR and infrared spectral data for Me2C=CHOD and Me2CDCHO are reported with some experimental details.

Homogeneous catalysis. Catalytic production of simple enols

Complexes of the type [Rh(diphosphine)(solvent)2]+ in dry acetone or tetrahydrofuran solutions are effective catalysts for generating synthetically useful quantities of simple enols from their corresponding allylic alcohols. A representative collection of simple enols has been produced, and the physical properties and stabilities are recorded. Although these catalysts also ketonize (tautomerize) the enols to their corresponding aldehydes and ketones, the simple enols are conveniently stable in solutions containing the milder catalysts. It is found that in the absence of catalyst simple enols are remarkably stable; the enols of propanal and methyl ethyl ketone persist for up to 2 weeks in dilute acetone solutions at 25 °C. The mechanism of catalysis has been inferred from specific isotopic labeling experiments. The conclusions are as follows: the production of enols involves a hydrogen 1,3-shift mechanism involving hydrido-π-allylic intermediates; the catalytic process is essentially irreversible; and the catalytic ketonization proceeds through a hydrido-π-oxyallylic intermediate. This process is also irreversible, and the stereoselective step is the α-hydrogen abstraction from the allylic substrate. The hydrogen abstraction is probably the turnover limiting step. Three examples of chemical reactions that are unique to enols are reported and are described as proceeding by an ene mechanism.

(E)- and (Z)-Prop-1-en-1-ol: Gas-phase Generation and Determination of Heats of Formation by Mass Spectrometry

The unstable (E)- and (Z)-prop-1-en-1-ol were generated in the gas phase and their heats of formation determined as -169 to -174 kJ mol-1.

Kinetics and Mechanism of the Decomposition of the Molecular Ions of Pentanal and its Monomethyl-substituted Homologues in the Picosecond to Microsecond Time Interval following Field Ionization

The kinetics of decomposition of pentanal and its monomethyl homologues, including hexanal, have been studied as a function of time following field ionisation (FI).With the aid of these results and other energetic measurements, the McLafferty rearrangement in the case of hexanal is shown to occur by a stepwise mechanism.