Structure and conversions of the condensation products of phenols with unsaturated carbonyl compounds

The reaction of 3,4-xylenol with crotonaldehyde leads to the formation of 2, 6, 7-trimethyl-4-(4, 5-dimethyl-2-hydroxyphenyl)chroman, whose structure is verified by IR and UV spectra, by the synthesis of the methyl and the benzoyl esters, and by the investigation of the conditions and the products of pyrolisis.The IR spectrum of a paste of IV in vaseline oil was recorded on a IKS-14 apparatus     

Phenylboronic acid mediated triple condensation reactions of phloroglucinol and unsaturated carbonyl compounds

[reaction: see text] A remarkable phenylboronic acid mediated triple condensation reaction of phloroglucinol (1,3,5-trihydroxybenzene) with a series of alpha,beta-unsaturated carbonyl compounds is reported. This experimentally simple reaction afforded novel C3-symmetric 2H-chromene derivatives. These derivatives represent structural analogues of the natural product xyloketal A, which has been reported to be a potent inhibitor of acetylcholine esterase.     

Synthesis of substituted phenols via 1,1-dichloro-2-nitroethene promoted condensation of carbonyl compounds with DMF

A novel and efficient metal-free synthesis of phenolic compounds was developed via coupling cyclization of DMF as a carbon source with active methylene compounds such as 1,3-dicarbonyl compounds with the assistance of 1,1-dichloro-2-nitroethene. The method we used was different from other traditional phenol functionalization methods. In the reaction, the 1,1-dichloro-2-nitroethene as a promoter which unlike our previous research on 1,1-dichloro-2-nitroethene. The method allows the convenient construction of phenolic compounds under mild reaction conditions and moderate yields.     

Epoxidation of unsaturated carbonyl compounds

Russian Journal of Organic Chemistry - Epoxidation of unsaturated carbonyl compounds by reaction with chloromethyl propargyl(allyl) ether in the presence of an alcoholate occurs exclusively at the...     

Features of the chromatography-mass spectrometric identification of condensation products of the carbonyl compounds

By the example of the condensation products of acetone with the simplest aromatic carbonyl compounds it was shown that the joint interpretation of mass spectrometric and chromatographic data in conjunction with a priori assumptions about the nature of the chemical structure allows the detection of the components of reaction mixtures that were not previously characterized by standard mass spectra or by retention indices on standard stationary phases. A necessary condition for solving such problems is creating a hypothesis about the sample composition that is possible for the expected products of the known organic reactions.     

Method for the condensation of diacetylene with carbonyl compounds

Conclusions A new method is proposed for the condensation of diacetylene with carbonyl compounds.Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 3, pp. 690–692, March, 1972.     

Structure of products of the reaction of 2-cyanoaziridine with carbonyl compounds

The structure of azimexone (3), the product of the reaction of 2-cyanoaziridine with acetone, was confirmed on the basis of¹H and¹³C NMR spectra. The formation of this product is accounted for by the -aziridinoalkylating action of an intermediate containing a good leaving iminoyloxy group. Similar reactions were observed for 1-chloromethylaziridine and a 1-aziridinylmethylammonium salt (6), but not for 1-methoxymethylaziridine (7) and 1-aziridinemethanol.Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 12, pp. 2136–2139, December, 1993.     

Intermediates in the reaction ofo-phenylenediamine with carbonyl compounds and their subsequent conversions

The reaction ofo-phenylenediamine with aldehydes and ketones has been studied using PMR spectroscopy. It has been established that the reaction begins with the formation of monoimines (isolated in condensations with aromatic aldehydes) which are cyclized to the corresponding benzimidazolines. The latter are converted in the reactions involving aldehydes and pinacolone into 2-substituted benzimidazoles, but with acetone and acetophenone give 2,3-dihydro-1H-benzo[b]-1,4-diazepine derivatives.Academy of Military Medicine, Saint Petersburg 194175, Russia. Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 3, pp. 363–367, March, 1998.     

Phosphazene base-catalyzed condensation of trimethylsilylacetate with carbonyl compounds

The t-Bu-P4 base was found to be an excellent catalyst for the condensation of trimethylsilylacetate or trimethylacetonitrile with carbonyl compounds to form functionalized alkenes and beta-enaminoesters were also synthesized by the condensation with formanilides.     

Combined interpretation of chromatographic and mass spectral information in identifying condensation products of carbonyl compounds

The paper considers one of possible approaches to the combined application of chromatographic and mass spectral data, based on the preliminary estimation of retention indices using additive schemes. This algorithm is used to determine structures of isomers formed in the condensation of carbonyl compounds (acetone and cyclohexanone) under basic catalysis.     

Nickel-catalyzed cycloaddition of unsaturated hydrocarbons and carbonyl compounds

A mild and general route for preparing pyrans and dienones from carbonyls and diynes is described. Ni imidazolylidene complexes were used to mediate cyclizations between diynes and aldehydes. The reaction of an enyne and an aldehyde afforded a mixture of cyclized products. In addition, a spiropyran was prepared from the cycloaddition of a diyne and cyclohexanone. [reaction: see text]     

Reactions of diazoalkanes with unsaturated compounds 15. Catalytic reactions of unsaturated carbonyl compounds and their derivatives with diazomethane

The present study concerned with the influence of the nature of the acetal fragment in unsaturated compounds on the reactivity of the C=C bond in cyclopropanation reactions with diazomethane catalyzed by copper and palladium compounds. The acetal substituents at the α- or γ-position with respect to the C=C bond were found to exert an activating effect on the yields of cyclopropanation products compared to the starting unsaturated carbonyl compounds, which give 1,3-dipolar cycloaddition adducts with CH₂N₂ as by-products. Cyclopropanation of the double bonds appeared to be most efficiently catalyzed by Pd(acac)₂. Dedicated to Corresponding Member of the Russian Academy of Sciences E. P. Serebryakov on the occasion of his 70th birthday. __________ Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 4, pp. 979–983, April, 2005.     

Anticorrosion properties of products of N-(2-Vinyloxyethyl)-1,2-ethylenediamine condensation with carbonyl compounds

N-(2-Vinyloxyethyl)-N′-cyclohexylidene-1,2-ethylenediamine and N,N′,N″-tris-[2-(2-vinyloxyethyl)-aminoethyl]hexahydro-1,3,5-triazine were synthesized by reactions of N-(2-vinyloxyethyl)-1,2-ethylenediamine with cyclohexanone and formaldehyde with yields of 91 and 90%, respectively. The IR and ¹H and ¹³C NMR spectral data and the results of studying their anticorrosion properties are given.     

Studies of the chemical conversions of unsaturated and high molecular weight compounds

Summary The concentration of the original monomers in the reaction medium influences the alteranation effect during the copolymerization of vinyl ethers with acrylates. A concentration of the active monomer may be chosen such that the polymer of methyl methacrylate will be formed at the beginning.     

The electronic structure of polyenes and unsaturated carbonyl compounds

PE spectra of polyene aldehydes are reported and discussed on the basis of a semiempirical LCFO-MO treatment within the π electron approximation. The necessary parameter values including the CC bond alternation were obtained by fitting PPP orbital and transition energies to the PE and UV data of diphenyl polyenes and polyene aldehydes. Thus, for planar systems the assignment of a PE band near 13.5 eV to the π orbital of the CO group could be given, which could be confirmed by the LCFO-MO calculations and by results from ab initio calculations, and which forms the basis of a discussion and comparison of π orbital interactions in planar unsaturated carbonyl compounds and hydrocarbons.