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Veliev, M. G.; Zhalobieva, A.Z.; Shatirova, M. I.; Mamedov, E. Sh.; Mamedov, I. M.

doi:10.1023/a:1012326912373

Cited by 5 publications

(2 citation statements)

References 2 publications

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“…The appearance of H 5 at ~3 ppm with characteristic coupling constants of ~9 and ~4 Hz to H 6 and H 6’ , respectively, unequivocally supports the assigned structures. These values are consistent with several endo -substituted derivatives (R = alkyl-like groups) reported by us [ 9 ] and others [ 21 – 22 ]. The observed selectivity is in agreement with the strong endo -selectivity displayed by diene 1 .…”

Section: Resultssupporting

confidence: 93%

Synthesis of oxa-bridged derivatives from Diels–Alder bis-adducts of butadiene and 1,2,3,4-tetrahalo-5,5-dimethoxycyclopentadiene

Khan

Parasuraman²

2010

Beilstein J. Org. Chem.

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Section: Resultssupporting

confidence: 93%

Synthesis of oxa-bridged derivatives from Diels–Alder bis-adducts of butadiene and 1,2,3,4-tetrahalo-5,5-dimethoxycyclopentadiene

Khan

Parasuraman²

2010

Beilstein J. Org. Chem.

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“…Modification with reactive acetylenic fragments enhances these properties. Interest in polyhalonorbornene derivatives is steadily growing, and new compounds of this class are being synthesized [4,5]. The presence of heavy halogen atoms extends the possibilities of structural studies of these compounds by IR and NMR spectroscopy and X-ray diffraction analysis [6 38].…”

mentioning

confidence: 99%

Acetylenic Esters of Polychlorobicyclo[2.2.1]hept-2-ene-5-carboxylic Acids

Mamedov

2005

Russ J Appl Chem

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Acetylenic esters of polychlorobicyclo[2.2.1]hept-2-ene-5-carboxylic acids were prepared from the corresponding acid chlorides and acetylenic alcohols.Polyhalonorbornenes are widely used in production of synthetic polyester resins with enhanced heat and flame resistance, epoxy resins, and additives to lubricating oils, and also as starting compounds in organic synthesis [133]. They exhibit fungicide, insecticide, and hebricide power and other kinds of biological activity. Modification with reactive acetylenic fragments enhances these properties. Interest in polyhalonorbornene derivatives is steadily growing, and new compounds of this class are being synthesized [4,5]. The presence of heavy halogen atoms extends the possibilities of structural studies of these compounds by IR and NMR spectroscopy and X-ray diffraction analysis [6 38].Acetylenic esters of bicyclo[2.2.1]hept-2-ene-5-carboxylic acids were studied in [9311]. In this study we developed preparation procedures and examined the structures of acetylenic esters of polychlorinated norbornenecarboxylic acids. These esters are prepared by the reactions of polychlorobicyclo[2.2.1]hept-2-ene-5-carboxylic acid chlorides with acetylenic alcohols. The starting chlorides V!VII were prepared by [4+2]-cycloaddition of chlorinated cyclopentadienes I!III to acryloyl chloride IV: I3III IV V3VII, where X = Cl (I, V), H (II, VI), OCH 3 (III, VII).The condensation of I!III with IV was performed at 100 3150oC for 10 315 h. The best results were obtained at 140oC, reaction time 10 h. Replacement of the geminal chlorine atoms by methoxy groups and hydrogen atoms favorably affects the reaction course; the yield of V!VII increases (see table).The 1 H NMR spectra show that compounds V!VII prepared under these conditions are exclusively endo isomers.Reactions of acid chlorides V!VII with alkynes VIII!X yielded the corresponding acetylenic esters of polychlorinated norbornenecarboxylic acids, XI!XIX: V3VII VIII3X XI3XIX , where R 1 = R 2 = H (VIII); R 1 = CH 3 , R 2 = H (IX); R 1 = CH 3 , R 2 = CH=CH 2 (X); R 1 = R 2 = H, X = Cl (XI); R 1 = CH 3 , R 2 = H, X = Cl (XII); R 1 = CH 3 , R 2 = CH=CH 2 , X = Cl (XIII); R 1 = R 2 = X = H (XIV); R 1 = CH 3 , R 2 = X = H (XV); R 1 = CH 3 , R 2 = CH=CH 2 , X = H (XVI); R 1 = R 2 = H, X = OCH 3 (XVII); R 1 = CH 3 , R 2 = H, X = OCH 3 (XVIII); R 1 = CH 3 , R 2 = CH=CH 2 , X = OCH 3 (XIX).The reaction was performed in organic solvents (diethyl ether, benzene) in the presence of tertiary amines (triethylamine, pyridine).The use of chlorides V!VII as starting compounds allows preparation of esters XI!XIX of high purity

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ChemInform Abstract: Diene Condensation of Polychlorocyclic Dienes with Dienophiles of Allylacetylene Series.

Veliev¹,

Chalobieva²,

Shatirova³

et al. 2001

ChemInform

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2001 cycloaddition reactions cycloaddition reactions O 0070 -043Diene Condensation of Polychlorocyclic Dienes with Dienophiles of Allylacetylene Series.-Cycloaddition of allylacetylenes (II) to polychlorocyclopentadienes (I) proceeds chemoselectively at the allyl double bond and with excellent diastereofacial selectivity to furnish the endo-propargyl adducts (III) in moderate to good yields. Some transformations of the adducts are studied. Reduction with Zn-Cu proceeds chemo-and stereoselectively to give E-allyl-substituted bicycloheptenes (VII). Favorsky decomposition of the tertiary alcohols in the side chain of compounds (III) can be selectively directed towards formation of the ethynyl [cf. (IV)] or allenyl group [cf. (V)]. -(VELIEV, M. G.; CHALOBIEVA, A. Z.; SHATIROVA, M. I.; MAMEDOV, E. SH.; MAMEDOV, I. M.; Russ.

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Untitled

Cited by 5 publications

References 2 publications

Synthesis of oxa-bridged derivatives from Diels–Alder bis-adducts of butadiene and 1,2,3,4-tetrahalo-5,5-dimethoxycyclopentadiene

Synthesis of oxa-bridged derivatives from Diels–Alder bis-adducts of butadiene and 1,2,3,4-tetrahalo-5,5-dimethoxycyclopentadiene

Acetylenic Esters of Polychlorobicyclo[2.2.1]hept-2-ene-5-carboxylic Acids

ChemInform Abstract: Diene Condensation of Polychlorocyclic Dienes with Dienophiles of Allylacetylene Series.

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