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Chiral propargylic cations as intermediates in SN1-type reactions: substitution pattern, nuclear magnetic resonance studies, and origin of the diastereoselectivity.

Journal of the American Chemical Society

Nitsch D, Huber SM, Pöthig A, Narayanan A, Olah GA, Prakash GK, Bach T.
PMID: 24494822
J Am Chem Soc. 2014 Feb 19;136(7):2851-7. doi: 10.1021/ja411772n. Epub 2014 Feb 04.

Nine propargylic acetates, bearing a stereogenic center (-C*HXR(2)) adjacent to the electrophilic carbon atom, were prepared and subjected to SN1-type substitution reactions with various silyl nucleophiles employing bismuth trifluoromethanesulfonate [Bi(OTf)3] as the Lewis acid. The diastereoselectivity of the reactions...

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Nitsch D, Huber SM, Pöthig A, et al. Chiral propargylic cations as intermediates in SN1-type reactions: substitution pattern, nuclear magnetic resonance studies, and origin of the diastereoselectivity. J Am Chem Soc. 2014;136(7):2851-7doi: 10.1021/ja411772n.
Nitsch, D., Huber, S. M., Pöthig, A., Narayanan, A., Olah, G. A., Prakash, G. K., & Bach, T. (2014). Chiral propargylic cations as intermediates in SN1-type reactions: substitution pattern, nuclear magnetic resonance studies, and origin of the diastereoselectivity. Journal of the American Chemical Society, 136(7), 2851-7. https://doi.org/10.1021/ja411772n
Nitsch, Dominik, et al. "Chiral propargylic cations as intermediates in SN1-type reactions: substitution pattern, nuclear magnetic resonance studies, and origin of the diastereoselectivity." Journal of the American Chemical Society vol. 136,7 (2014): 2851-7. doi: https://doi.org/10.1021/ja411772n
Nitsch D, Huber SM, Pöthig A, Narayanan A, Olah GA, Prakash GK, Bach T. Chiral propargylic cations as intermediates in SN1-type reactions: substitution pattern, nuclear magnetic resonance studies, and origin of the diastereoselectivity. J Am Chem Soc. 2014 Feb 19;136(7):2851-7. doi: 10.1021/ja411772n. Epub 2014 Feb 04. PMID: 24494822.
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Mammalian exocrine secretions: X. constituents of preorbital secretion of grysbok,Raphicerus melanotis.

Journal of chemical ecology

Burger BV, Tien FC, Le Roux M, Mo WP.
PMID: 24227582
J Chem Ecol. 1996 Apr;22(4):739-64. doi: 10.1007/BF02033583.

Using electron impact and chemical ionization mass spectrometry with methane and nitric oxide as reactant gases in conjunction with mass spectral analysis of the dimethyl disulfide derivatives of unsaturated constituents, 51 compounds have been identified in addition to the...

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Burger BV, Tien FC, Le Roux M, et al. Mammalian exocrine secretions: X. constituents of preorbital secretion of grysbok,Raphicerus melanotis. J Chem Ecol. 1996;22(4):739-64doi: 10.1007/BF02033583.
Burger, B. V., Tien, F. C., Le Roux, M., & Mo, W. P. (1996). Mammalian exocrine secretions: X. constituents of preorbital secretion of grysbok,Raphicerus melanotis. Journal of chemical ecology, 22(4), 739-64. https://doi.org/10.1007/BF02033583
Burger, B V, et al. "Mammalian exocrine secretions: X. constituents of preorbital secretion of grysbok,Raphicerus melanotis." Journal of chemical ecology vol. 22,4 (1996): 739-64. doi: https://doi.org/10.1007/BF02033583
Burger BV, Tien FC, Le Roux M, Mo WP. Mammalian exocrine secretions: X. constituents of preorbital secretion of grysbok,Raphicerus melanotis. J Chem Ecol. 1996 Apr;22(4):739-64. doi: 10.1007/BF02033583. PMID: 24227582.
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Sex pheromone of tomato pestScrobipalpuloides absoluta (Lepidoptera: Gelechiidae).

Journal of chemical ecology

Svatoš A, Attygalle AB, Jham GN, Frighetto RT, Vilela EF, Saman D, Meinwald J.
PMID: 24227585
J Chem Ecol. 1996 Apr;22(4):787-800. doi: 10.1007/BF02033586.

The sex attractant ofScrobipalpuloides absoluta females is a 90:10 mixture of (3E,8Z,11Z)-3,8,11-tetradecatrien-1-yl acetate and (3E,8Z)-3,8-tetradecadien-1-yl acetate. Tetradecadienyl acetates bearing 8Z,11Z; 3E,8Z; and 3E,11Z double bonds were synthesized by stereospecific procedures; the mass spectral and gas chromatographic properties of the...

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Svatoš A, Attygalle AB, Jham GN, et al. Sex pheromone of tomato pestScrobipalpuloides absoluta (Lepidoptera: Gelechiidae). J Chem Ecol. 1996;22(4):787-800doi: 10.1007/BF02033586.
Svatoš, A., Attygalle, A. B., Jham, G. N., Frighetto, R. T., Vilela, E. F., Saman, D., & Meinwald, J. (1996). Sex pheromone of tomato pestScrobipalpuloides absoluta (Lepidoptera: Gelechiidae). Journal of chemical ecology, 22(4), 787-800. https://doi.org/10.1007/BF02033586
Svatoš, A, et al. "Sex pheromone of tomato pestScrobipalpuloides absoluta (Lepidoptera: Gelechiidae)." Journal of chemical ecology vol. 22,4 (1996): 787-800. doi: https://doi.org/10.1007/BF02033586
Svatoš A, Attygalle AB, Jham GN, Frighetto RT, Vilela EF, Saman D, Meinwald J. Sex pheromone of tomato pestScrobipalpuloides absoluta (Lepidoptera: Gelechiidae). J Chem Ecol. 1996 Apr;22(4):787-800. doi: 10.1007/BF02033586. PMID: 24227585.
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Nickel-Mediated Asymmetric Allylic Alkylation between Nitroallylic Acetates and Acyl Imidazoles.

Organic letters

Wang J, Wang P, Wang L, Li D, Wang K, Wang Y, Zhu H, Yang D, Wang R.
PMID: 28862455
Org Lett. 2017 Sep 15;19(18):4826-4829. doi: 10.1021/acs.orglett.7b02264. Epub 2017 Sep 01.

A nickel-mediated asymmetric allylic alkylation reaction between imidazole-modified ketones and nitroallylic acetates is presented. This reaction is catalyzed by a simple chiral diamine-nickel catalyst under mild conditions and leads to a series of novel enantioenriched α-allylic adducts in moderate...

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Wang J, Wang P, Wang L, et al. Nickel-Mediated Asymmetric Allylic Alkylation between Nitroallylic Acetates and Acyl Imidazoles. Org Lett. 2017;19(18):4826-4829doi: 10.1021/acs.orglett.7b02264.
Wang, J., Wang, P., Wang, L., Li, D., Wang, K., Wang, Y., Zhu, H., Yang, D., & Wang, R. (2017). Nickel-Mediated Asymmetric Allylic Alkylation between Nitroallylic Acetates and Acyl Imidazoles. Organic letters, 19(18), 4826-4829. https://doi.org/10.1021/acs.orglett.7b02264
Wang, Jie, et al. "Nickel-Mediated Asymmetric Allylic Alkylation between Nitroallylic Acetates and Acyl Imidazoles." Organic letters vol. 19,18 (2017): 4826-4829. doi: https://doi.org/10.1021/acs.orglett.7b02264
Wang J, Wang P, Wang L, Li D, Wang K, Wang Y, Zhu H, Yang D, Wang R. Nickel-Mediated Asymmetric Allylic Alkylation between Nitroallylic Acetates and Acyl Imidazoles. Org Lett. 2017 Sep 15;19(18):4826-4829. doi: 10.1021/acs.orglett.7b02264. Epub 2017 Sep 01. PMID: 28862455.
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Diastereoselective synthesis of spiro[benzo[d]pyrrolo[2,1-b]thiazole-3,3'-indolines] via cycloaddition reaction of N-phenacylbenzothiazolium bromides and 3-methyleneoxindoles.

Organic & biomolecular chemistry

Shen GL, Sun J, Yan CG.
PMID: 26373777
Org Biomol Chem. 2015 Nov 28;13(44):10929-38. doi: 10.1039/c5ob01374g. Epub 2015 Sep 16.

The domino cycloaddition reactions of N-phenacylbenzothiazolium bromides with 3-phenacylideneoxindoles or ethyl 2-(2-oxoindolin-3-ylidene)acetates in ethanol at room temperature in the presence of triethylamine as a base afforded functionalized spiro[benzo[d]pyrrolo[2,1-b]thiazole-3,3'-indolines] in good yields and with high diastereoselectivity. The similar reactions of...

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Shen GL, Sun J, Yan CG. Diastereoselective synthesis of spiro[benzo[d]pyrrolo[2,1-b]thiazole-3,3'-indolines] via cycloaddition reaction of N-phenacylbenzothiazolium bromides and 3-methyleneoxindoles. Org Biomol Chem. 2015;13(44):10929-38doi: 10.1039/c5ob01374g.
Shen, G. L., Sun, J., & Yan, C. G. (2015). Diastereoselective synthesis of spiro[benzo[d]pyrrolo[2,1-b]thiazole-3,3'-indolines] via cycloaddition reaction of N-phenacylbenzothiazolium bromides and 3-methyleneoxindoles. Organic & biomolecular chemistry, 13(44), 10929-38. https://doi.org/10.1039/c5ob01374g
Shen, Guo-Liang, et al. "Diastereoselective synthesis of spiro[benzo[d]pyrrolo[2,1-b]thiazole-3,3'-indolines] via cycloaddition reaction of N-phenacylbenzothiazolium bromides and 3-methyleneoxindoles." Organic & biomolecular chemistry vol. 13,44 (2015): 10929-38. doi: https://doi.org/10.1039/c5ob01374g
Shen GL, Sun J, Yan CG. Diastereoselective synthesis of spiro[benzo[d]pyrrolo[2,1-b]thiazole-3,3'-indolines] via cycloaddition reaction of N-phenacylbenzothiazolium bromides and 3-methyleneoxindoles. Org Biomol Chem. 2015 Nov 28;13(44):10929-38. doi: 10.1039/c5ob01374g. Epub 2015 Sep 16. PMID: 26373777.
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Pd-Catalyzed oxidative isomerization of propargylic acetates: highly efficient access to α-acetoxyenones via alkenyl Csp(2)-O bond-forming reductive elimination from Pd(IV).

Chemical communications (Cambridge, England)

Li J, Yang W, Yan F, Liu Q, Wang P, Li Y, Zhao Y, Dong Y, Liu H.
PMID: 27500292
Chem Commun (Camb). 2016 Aug 23;52(70):10644-7. doi: 10.1039/c6cc04463h.

A Pd(ii)/(iv)-catalyzed oxidative isomerization of propargylic acetates developed for the synthesis of polysubstituted alkenyl acetates is described. The reductive elimination of alkenyl Csp(2)-OAc bonds from Pd(IV) intermediates is achieved. Mechanistic studies indicate that the reaction mechanism consists of trans...

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Li J, Yang W, Yan F, et al. Pd-Catalyzed oxidative isomerization of propargylic acetates: highly efficient access to α-acetoxyenones via alkenyl Csp(2)-O bond-forming reductive elimination from Pd(IV). Chem Commun (Camb). 2016;52(70):10644-7doi: 10.1039/c6cc04463h.
Li, J., Yang, W., Yan, F., Liu, Q., Wang, P., Li, Y., Zhao, Y., Dong, Y., & Liu, H. (2016). Pd-Catalyzed oxidative isomerization of propargylic acetates: highly efficient access to α-acetoxyenones via alkenyl Csp(2)-O bond-forming reductive elimination from Pd(IV). Chemical communications (Cambridge, England), 52(70), 10644-7. https://doi.org/10.1039/c6cc04463h
Li, Jun, et al. "Pd-Catalyzed oxidative isomerization of propargylic acetates: highly efficient access to α-acetoxyenones via alkenyl Csp(2)-O bond-forming reductive elimination from Pd(IV)." Chemical communications (Cambridge, England) vol. 52,70 (2016): 10644-7. doi: https://doi.org/10.1039/c6cc04463h
Li J, Yang W, Yan F, Liu Q, Wang P, Li Y, Zhao Y, Dong Y, Liu H. Pd-Catalyzed oxidative isomerization of propargylic acetates: highly efficient access to α-acetoxyenones via alkenyl Csp(2)-O bond-forming reductive elimination from Pd(IV). Chem Commun (Camb). 2016 Aug 23;52(70):10644-7. doi: 10.1039/c6cc04463h. PMID: 27500292.
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A One-Pot Assembly of Fully Substituted Alkyl 5-Aminothiophene-2-carboxylates from Allenes, Isothiocyanates, and Alkyl 2-Bromoacetates.

The Journal of organic chemistry

Nedolya NA, Tarasova OA, Albanov AI, Trofimov BA.
PMID: 28636379
J Org Chem. 2017 Jul 21;82(14):7519-7528. doi: 10.1021/acs.joc.7b01217. Epub 2017 Jul 05.

A novel simple approach to highly functionalized multisubstituted thiophenes such as alkyl 4-alkoxy-5-amino-3-methylthiophene-2-carboxylates through the one-pot sequential reaction of α-lithiated alkoxyallenes with isothiocyanates and alkyl 2-bromoacetates has been discovered. The process proceeds quickly (30-45 min) via in situ formation...

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Nedolya NA, Tarasova OA, Albanov AI, et al. A One-Pot Assembly of Fully Substituted Alkyl 5-Aminothiophene-2-carboxylates from Allenes, Isothiocyanates, and Alkyl 2-Bromoacetates. J Org Chem. 2017;82(14):7519-7528doi: 10.1021/acs.joc.7b01217.
Nedolya, N. A., Tarasova, O. A., Albanov, A. I., & Trofimov, B. A. (2017). A One-Pot Assembly of Fully Substituted Alkyl 5-Aminothiophene-2-carboxylates from Allenes, Isothiocyanates, and Alkyl 2-Bromoacetates. The Journal of organic chemistry, 82(14), 7519-7528. https://doi.org/10.1021/acs.joc.7b01217
Nedolya, Nina A, et al. "A One-Pot Assembly of Fully Substituted Alkyl 5-Aminothiophene-2-carboxylates from Allenes, Isothiocyanates, and Alkyl 2-Bromoacetates." The Journal of organic chemistry vol. 82,14 (2017): 7519-7528. doi: https://doi.org/10.1021/acs.joc.7b01217
Nedolya NA, Tarasova OA, Albanov AI, Trofimov BA. A One-Pot Assembly of Fully Substituted Alkyl 5-Aminothiophene-2-carboxylates from Allenes, Isothiocyanates, and Alkyl 2-Bromoacetates. J Org Chem. 2017 Jul 21;82(14):7519-7528. doi: 10.1021/acs.joc.7b01217. Epub 2017 Jul 05. PMID: 28636379.
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Practical Stannylation of Allyl Acetates Catalyzed by Nickel with Bu3 SnOMe.

Chemistry (Weinheim an der Bergstrasse, Germany)

Komeyama K, Itai Y, Takaki K.
PMID: 27124370
Chemistry. 2016 Jun 27;22(27):9130-4. doi: 10.1002/chem.201601515. Epub 2016 May 25.

A practical and scalable nickel-catalyzed allylic stannylation of allyl acetates with Bu3 SnOMe is described. A variety of acyclic and cyclic allyl acetates, even with base-sensitive moieties, undergoes the stannylation by using NiBr2 /4,4'-di-tert-butylbipyridine (dtbpy)/Mn catalyst system to afford...

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Komeyama K, Itai Y, Takaki K. Practical Stannylation of Allyl Acetates Catalyzed by Nickel with Bu3 SnOMe. Chemistry. 2016;22(27):9130-4doi: 10.1002/chem.201601515.
Komeyama, K., Itai, Y., & Takaki, K. (2016). Practical Stannylation of Allyl Acetates Catalyzed by Nickel with Bu3 SnOMe. Chemistry (Weinheim an der Bergstrasse, Germany), 22(27), 9130-4. https://doi.org/10.1002/chem.201601515
Komeyama, Kimihiro, et al. "Practical Stannylation of Allyl Acetates Catalyzed by Nickel with Bu3 SnOMe." Chemistry (Weinheim an der Bergstrasse, Germany) vol. 22,27 (2016): 9130-4. doi: https://doi.org/10.1002/chem.201601515
Komeyama K, Itai Y, Takaki K. Practical Stannylation of Allyl Acetates Catalyzed by Nickel with Bu3 SnOMe. Chemistry. 2016 Jun 27;22(27):9130-4. doi: 10.1002/chem.201601515. Epub 2016 May 25. PMID: 27124370.
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Response specificity of male pink bollworm moths to different blends and dosages of sex pheromone.

Journal of chemical ecology

Linn CE, Roelofs WL.
PMID: 24311250
J Chem Ecol. 1985 Nov;11(11):1583-90. doi: 10.1007/BF01012203.

Male pink bollworm,Pectinophora gossypiella, were tested in a sustained flight tunnel to 119 blend-dosage combinations of the sex pheromone components, (Z,Z)- and (Z,E)-7,11-hexadecadienyl acetates, which are released by conspecific females in a 61∶39 ratio. Hierarchical cluster analysis was used...

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Linn CE, Roelofs WL. Response specificity of male pink bollworm moths to different blends and dosages of sex pheromone. J Chem Ecol. 1985;11(11):1583-90doi: 10.1007/BF01012203.
Linn, C. E., & Roelofs, W. L. (1985). Response specificity of male pink bollworm moths to different blends and dosages of sex pheromone. Journal of chemical ecology, 11(11), 1583-90. https://doi.org/10.1007/BF01012203
Linn, C E, and Roelofs, W L. "Response specificity of male pink bollworm moths to different blends and dosages of sex pheromone." Journal of chemical ecology vol. 11,11 (1985): 1583-90. doi: https://doi.org/10.1007/BF01012203
Linn CE, Roelofs WL. Response specificity of male pink bollworm moths to different blends and dosages of sex pheromone. J Chem Ecol. 1985 Nov;11(11):1583-90. doi: 10.1007/BF01012203. PMID: 24311250.
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Aldehydic contact poisons and alarm pheromone of the antCrematogaster scutellaris (Hymenoptera: Myrmicinae) : Enzyme-Mediated Production from acetate precursors.

Journal of chemical ecology

Pasteels JM, Daloze D, Boeve JL.
PMID: 24272094
J Chem Ecol. 1989 May;15(5):1501-11. doi: 10.1007/BF01012379.

The Dufour gland ofCrematogaster scutellaris stores a mixture of long-chain primary acetates bearing a cross-conjugated dienone (Scheme 1, la-c). The poison gland contains two highly active enzymes: an acetate esterase and an alcohol oxidase. During venom emission, the constituents...

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Pasteels JM, Daloze D, Boeve JL. Aldehydic contact poisons and alarm pheromone of the antCrematogaster scutellaris (Hymenoptera: Myrmicinae) : Enzyme-Mediated Production from acetate precursors. J Chem Ecol. 1989;15(5):1501-11doi: 10.1007/BF01012379.
Pasteels, J. M., Daloze, D., & Boeve, J. L. (1989). Aldehydic contact poisons and alarm pheromone of the antCrematogaster scutellaris (Hymenoptera: Myrmicinae) : Enzyme-Mediated Production from acetate precursors. Journal of chemical ecology, 15(5), 1501-11. https://doi.org/10.1007/BF01012379
Pasteels, J M, et al. "Aldehydic contact poisons and alarm pheromone of the antCrematogaster scutellaris (Hymenoptera: Myrmicinae) : Enzyme-Mediated Production from acetate precursors." Journal of chemical ecology vol. 15,5 (1989): 1501-11. doi: https://doi.org/10.1007/BF01012379
Pasteels JM, Daloze D, Boeve JL. Aldehydic contact poisons and alarm pheromone of the antCrematogaster scutellaris (Hymenoptera: Myrmicinae) : Enzyme-Mediated Production from acetate precursors. J Chem Ecol. 1989 May;15(5):1501-11. doi: 10.1007/BF01012379. PMID: 24272094.
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Intraspecific variation and interspecific differences in sex pheromones of sibling species inCtenopseustis obliquana complex.

Journal of chemical ecology

Clearwater JR, Foster SP, Muggleston SJ, Dugdale JS, Priesner E.
PMID: 24258735
J Chem Ecol. 1991 Feb;17(2):413-29. doi: 10.1007/BF00994342.

The specific status ofCtenopseustis obliquana pheromone-types I, II, and III has been more fully examined. Females of types I and III produce a mixture of (Z)-8- and (Z)-5-tetradecenyl acetates (Z8-14:Ac, Z5-14: Ac). The previously reported different ratios of these...

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Clearwater JR, Foster SP, Muggleston SJ, et al. Intraspecific variation and interspecific differences in sex pheromones of sibling species inCtenopseustis obliquana complex. J Chem Ecol. 1991;17(2):413-29doi: 10.1007/BF00994342.
Clearwater, J. R., Foster, S. P., Muggleston, S. J., Dugdale, J. S., & Priesner, E. (1991). Intraspecific variation and interspecific differences in sex pheromones of sibling species inCtenopseustis obliquana complex. Journal of chemical ecology, 17(2), 413-29. https://doi.org/10.1007/BF00994342
Clearwater, J R, et al. "Intraspecific variation and interspecific differences in sex pheromones of sibling species inCtenopseustis obliquana complex." Journal of chemical ecology vol. 17,2 (1991): 413-29. doi: https://doi.org/10.1007/BF00994342
Clearwater JR, Foster SP, Muggleston SJ, Dugdale JS, Priesner E. Intraspecific variation and interspecific differences in sex pheromones of sibling species inCtenopseustis obliquana complex. J Chem Ecol. 1991 Feb;17(2):413-29. doi: 10.1007/BF00994342. PMID: 24258735.
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Neutral compounds from male castoreum of North American beaver,Castor canadensis.

Journal of chemical ecology

Tang R, Webster FX, Müller-Schwarze D.
PMID: 24233827
J Chem Ecol. 1995 Nov;21(11):1745-62. doi: 10.1007/BF02033674.

North American beavers (Castor canadensis) mark their territories with castoreum, the strong-smelling paste in their castor sacs. In their own territories, beavers respond with scent marking to experimental scent marks that consist of strange castoreum (or selected components). In...

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Tang R, Webster FX, Müller-Schwarze D. Neutral compounds from male castoreum of North American beaver,Castor canadensis. J Chem Ecol. 1995;21(11):1745-62doi: 10.1007/BF02033674.
Tang, R., Webster, F. X., & Müller-Schwarze, D. (1995). Neutral compounds from male castoreum of North American beaver,Castor canadensis. Journal of chemical ecology, 21(11), 1745-62. https://doi.org/10.1007/BF02033674
Tang, R, et al. "Neutral compounds from male castoreum of North American beaver,Castor canadensis." Journal of chemical ecology vol. 21,11 (1995): 1745-62. doi: https://doi.org/10.1007/BF02033674
Tang R, Webster FX, Müller-Schwarze D. Neutral compounds from male castoreum of North American beaver,Castor canadensis. J Chem Ecol. 1995 Nov;21(11):1745-62. doi: 10.1007/BF02033674. PMID: 24233827.
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Showing 1 to 12 of 856 entries