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Preparation of new chiral borane-protected P,N-ferrocenyl ligands via a methoxy directed ortho-lithiation.

Chirality

Lotz M, Ireland T, Tappe K, Knochel P.
PMID: 10824158
Chirality. 2000 Jun;12(5):389-95. doi: 10.1002/(SICI)1520-636X(2000)12:5/6<389::AID-CHIR16>3.0.CO;2-S.

We have shown that the readily prepared (ferrocenyl)benzylic methyl ethers of type 1 can be ortho-metalated with tert-BuLi with high diastereoselectivity. This reaction has been used to prepare new borane-protected P,N-substituted ferrocenes of type 2 in high diastereomeric and...

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Lotz M, Ireland T, Tappe K, et al. Preparation of new chiral borane-protected P,N-ferrocenyl ligands via a methoxy directed ortho-lithiation. Chirality. 2000;12(5):389-95doi: 10.1002/(SICI)1520-636X(2000)12:5/6<389::AID-CHIR16>3.0.CO;2-S.
Lotz, M., Ireland, T., Tappe, K., & Knochel, P. (2000). Preparation of new chiral borane-protected P,N-ferrocenyl ligands via a methoxy directed ortho-lithiation. Chirality, 12(5), 389-95. https://doi.org/10.1002/(SICI)1520-636X(2000)12:5/6<389::AID-CHIR16>3.0.CO;2-S
Lotz, M, et al. "Preparation of new chiral borane-protected P,N-ferrocenyl ligands via a methoxy directed ortho-lithiation." Chirality vol. 12,5 (2000): 389-95. doi: https://doi.org/10.1002/(SICI)1520-636X(2000)12:5/6<389::AID-CHIR16>3.0.CO;2-S
Lotz M, Ireland T, Tappe K, Knochel P. Preparation of new chiral borane-protected P,N-ferrocenyl ligands via a methoxy directed ortho-lithiation. Chirality. 2000 Jun;12(5):389-95. doi: 10.1002/(SICI)1520-636X(2000)12:5/6<389::AID-CHIR16>3.0.CO;2-S. PMID: 10824158.
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Nucleophilic epoxidation of gamma-hydroxyvinyl sulfoxide derivatives.

The Journal of organic chemistry

Fernández de la Pradilla R, Buergo MV, Manzano P, Montero C, Priego J, Viso A, Cano FH, Martínez-Alcázar MP.
PMID: 12790584
J Org Chem. 2003 Jun 13;68(12):4797-805. doi: 10.1021/jo0342828.

The nucleophilic epoxidation of simple (gamma-silyloxy)vinyl sulfoxides takes place with complete stereocontrol and high yields. For substrates bearing an additional substituent at the gamma position, a reinforcing/nonreinforcing scenario is operative. While E and Z silylated substrates undergo a primarily...

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Fernández de la Pradilla R, Buergo MV, Manzano P, et al. Nucleophilic epoxidation of gamma-hydroxyvinyl sulfoxide derivatives. J Org Chem. 2003;68(12):4797-805doi: 10.1021/jo0342828.
Fernández de la Pradilla, R., Buergo, M. V., Manzano, P., Montero, C., Priego, J., Viso, A., Cano, F. H., & Martínez-Alcázar, M. P. (2003). Nucleophilic epoxidation of gamma-hydroxyvinyl sulfoxide derivatives. The Journal of organic chemistry, 68(12), 4797-805. https://doi.org/10.1021/jo0342828
Fernández de la Pradilla, Roberto, et al. "Nucleophilic epoxidation of gamma-hydroxyvinyl sulfoxide derivatives." The Journal of organic chemistry vol. 68,12 (2003): 4797-805. doi: https://doi.org/10.1021/jo0342828
Fernández de la Pradilla R, Buergo MV, Manzano P, Montero C, Priego J, Viso A, Cano FH, Martínez-Alcázar MP. Nucleophilic epoxidation of gamma-hydroxyvinyl sulfoxide derivatives. J Org Chem. 2003 Jun 13;68(12):4797-805. doi: 10.1021/jo0342828. PMID: 12790584.
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Intramolecular proton transfers in stereoisomeric gas-phase ions and the kinetic nature of the protonation process upon chemical ionization .

Journal of mass spectrometry : JMS

Vais V, Etinger A, Mandelbaum A.
PMID: 10407360
J Mass Spectrom. 1999 Jul;34(7):755-60. doi: 10.1002/(SICI)1096-9888(199907)34:7<755::AID-JMS831>3.0.CO;2-J.

The isobutane chemical ionization (CI) mass spectra of cis- and trans-1-butyl-3- and -4-dimethylaminocyclohexanols and of their methyl ethers exhibit abundant [MH - H(2)O](+) and [MH - MeOH](+) ions respectively. On the other hand, only the MH(+) ions of the...

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Vais V, Etinger A, Mandelbaum A. Intramolecular proton transfers in stereoisomeric gas-phase ions and the kinetic nature of the protonation process upon chemical ionization . J Mass Spectrom. 1999;34(7):755-60doi: 10.1002/(SICI)1096-9888(199907)34:7<755::AID-JMS831>3.0.CO;2-J.
Vais, V., Etinger, A., & Mandelbaum, A. (1999). Intramolecular proton transfers in stereoisomeric gas-phase ions and the kinetic nature of the protonation process upon chemical ionization . Journal of mass spectrometry : JMS, 34(7), 755-60. https://doi.org/10.1002/(SICI)1096-9888(199907)34:7<755::AID-JMS831>3.0.CO;2-J
Vais, et al. "Intramolecular proton transfers in stereoisomeric gas-phase ions and the kinetic nature of the protonation process upon chemical ionization ." Journal of mass spectrometry : JMS vol. 34,7 (1999): 755-60. doi: https://doi.org/10.1002/(SICI)1096-9888(199907)34:7<755::AID-JMS831>3.0.CO;2-J
Vais V, Etinger A, Mandelbaum A. Intramolecular proton transfers in stereoisomeric gas-phase ions and the kinetic nature of the protonation process upon chemical ionization . J Mass Spectrom. 1999 Jul;34(7):755-60. doi: 10.1002/(SICI)1096-9888(199907)34:7<755::AID-JMS831>3.0.CO;2-J. PMID: 10407360.
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Carbon-13 NMR spectroscopic studies on chemically modified and unmodified synthetic and natural humic acids.

Talanta

Sachs S, Bubner M, Schmeide K, Choppin GR, Heise KH, Bernhard G.
PMID: 18968705
Talanta. 2002 Jul 03;57(5):999-1009. doi: 10.1016/s0039-9140(02)00140-6.

Carbon-13 cross-polarization magic-angle spinning nuclear magnetic resonance spectroscopy ((13)C-CP/MAS-NMR) was applied to study the chemical modification process of humic acids (HA) with diazomethane and the subsequent alkaline hydrolysis of the methylated HA. This modification process results in HA with...

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Sachs S, Bubner M, Schmeide K, et al. Carbon-13 NMR spectroscopic studies on chemically modified and unmodified synthetic and natural humic acids. Talanta. 2002;57(5):999-1009doi: 10.1016/s0039-9140(02)00140-6.
Sachs, S., Bubner, M., Schmeide, K., Choppin, G. R., Heise, K. H., & Bernhard, G. (2002). Carbon-13 NMR spectroscopic studies on chemically modified and unmodified synthetic and natural humic acids. Talanta, 57(5), 999-1009. https://doi.org/10.1016/s0039-9140(02)00140-6
Sachs, S, et al. "Carbon-13 NMR spectroscopic studies on chemically modified and unmodified synthetic and natural humic acids." Talanta vol. 57,5 (2002): 999-1009. doi: https://doi.org/10.1016/s0039-9140(02)00140-6
Sachs S, Bubner M, Schmeide K, Choppin GR, Heise KH, Bernhard G. Carbon-13 NMR spectroscopic studies on chemically modified and unmodified synthetic and natural humic acids. Talanta. 2002 Jul 03;57(5):999-1009. doi: 10.1016/s0039-9140(02)00140-6. PMID: 18968705.
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In situ nucleophilic substitution reaction of N,N-dialkylaminoethyl-2-chlorides monitored by gas chromatography/mass spectrometry.

Rapid communications in mass spectrometry : RCM

Lakshmi VV, Reddy TJ, Murty MR, Prabhakar S, Vairamani M.
PMID: 16791867
Rapid Commun Mass Spectrom. 2006;20(14):2209-14. doi: 10.1002/rcm.2581.

The detection and identification of degradation products of scheduled chemicals, which are characteristic markers of Chemical Warfare agents (CWAs), plays a key role in verification analysis. Identification of such non-scheduled but specific markers of CWAs helps in deciphering the...

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Lakshmi VV, Reddy TJ, Murty MR, et al. In situ nucleophilic substitution reaction of N,N-dialkylaminoethyl-2-chlorides monitored by gas chromatography/mass spectrometry. Rapid Commun Mass Spectrom. 2006;20(14):2209-14doi: 10.1002/rcm.2581.
Lakshmi, V. V., Reddy, T. J., Murty, M. R., Prabhakar, S., & Vairamani, M. (2006). In situ nucleophilic substitution reaction of N,N-dialkylaminoethyl-2-chlorides monitored by gas chromatography/mass spectrometry. Rapid communications in mass spectrometry : RCM, 20(14), 2209-14. https://doi.org/10.1002/rcm.2581
Lakshmi, V V S, et al. "In situ nucleophilic substitution reaction of N,N-dialkylaminoethyl-2-chlorides monitored by gas chromatography/mass spectrometry." Rapid communications in mass spectrometry : RCM vol. 20,14 (2006): 2209-14. doi: https://doi.org/10.1002/rcm.2581
Lakshmi VV, Reddy TJ, Murty MR, Prabhakar S, Vairamani M. In situ nucleophilic substitution reaction of N,N-dialkylaminoethyl-2-chlorides monitored by gas chromatography/mass spectrometry. Rapid Commun Mass Spectrom. 2006;20(14):2209-14. doi: 10.1002/rcm.2581. PMID: 16791867.
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Synthesis of diazacalix[8]arene and triazacalix[12]arene methyl ethers via intramolecular aryl amination.

Organic letters

Lawson KV, Barton AC, Spence JD.
PMID: 19152313
Org Lett. 2009 Feb 19;11(4):895-8. doi: 10.1021/ol8028912.

Azacalixarenes derived from p-tert-butylphenol are generated by an intramolecular aryl amination strategy as the ring-closing step. The reaction produces the first examples of larger p-tert-butylcalixarenes with regioselective substitution of bridging methylenes with nitrogen atoms.

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Lawson KV, Barton AC, Spence JD. Synthesis of diazacalix[8]arene and triazacalix[12]arene methyl ethers via intramolecular aryl amination. Org Lett. 2009;11(4):895-8doi: 10.1021/ol8028912.
Lawson, K. V., Barton, A. C., & Spence, J. D. (2009). Synthesis of diazacalix[8]arene and triazacalix[12]arene methyl ethers via intramolecular aryl amination. Organic letters, 11(4), 895-8. https://doi.org/10.1021/ol8028912
Lawson, Kenneth V, et al. "Synthesis of diazacalix[8]arene and triazacalix[12]arene methyl ethers via intramolecular aryl amination." Organic letters vol. 11,4 (2009): 895-8. doi: https://doi.org/10.1021/ol8028912
Lawson KV, Barton AC, Spence JD. Synthesis of diazacalix[8]arene and triazacalix[12]arene methyl ethers via intramolecular aryl amination. Org Lett. 2009 Feb 19;11(4):895-8. doi: 10.1021/ol8028912. PMID: 19152313.
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Hydroxymethylaniline Photocages for Carboxylic Acids and Alcohols.

The Journal of organic chemistry

Škalamera Đ, Blažek Bregović V, Antol I, Bohne C, Basarić N.
PMID: 29119784
J Org Chem. 2017 Dec 01;82(23):12554-12568. doi: 10.1021/acs.joc.7b02314. Epub 2017 Nov 20.

ortho-, meta- and para-Hydroxymethylaniline methyl ethers 3-5-OMe and acetyl derivatives 3-5-OAc were investigated as potential photocages for alcohols and carboxylic acids, respectively. The measurements of photohydrolysis efficiency showed that the decaging from ortho- and meta-derivatives takes place efficiently in...

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Škalamera Đ, Blažek Bregović V, Antol I, et al. Hydroxymethylaniline Photocages for Carboxylic Acids and Alcohols. J Org Chem. 2017;82(23):12554-12568doi: 10.1021/acs.joc.7b02314.
Škalamera, �. �., Blažek Bregović, V., Antol, I., Bohne, C., & Basarić, N. (2017). Hydroxymethylaniline Photocages for Carboxylic Acids and Alcohols. The Journal of organic chemistry, 82(23), 12554-12568. https://doi.org/10.1021/acs.joc.7b02314
Škalamera, Đani, et al. "Hydroxymethylaniline Photocages for Carboxylic Acids and Alcohols." The Journal of organic chemistry vol. 82,23 (2017): 12554-12568. doi: https://doi.org/10.1021/acs.joc.7b02314
Škalamera Đ, Blažek Bregović V, Antol I, Bohne C, Basarić N. Hydroxymethylaniline Photocages for Carboxylic Acids and Alcohols. J Org Chem. 2017 Dec 01;82(23):12554-12568. doi: 10.1021/acs.joc.7b02314. Epub 2017 Nov 20. PMID: 29119784.
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Reversible double C-H bond activation of linear and cyclic ethers to form iridium carbenes.

Chemistry (Weinheim an der Bergstrasse, Germany)

Valpuesta JE, Álvarez E, López-Serrano J, Maya C, Carmona E.
PMID: 22962021
Chemistry. 2012 Oct 08;18(41):13149-59. doi: 10.1002/chem.201201883. Epub 2012 Sep 07.

The double C-H bond activation of a series of linear and cyclic ethers by the iridium complex [Tp(tol')Ir(C(6)H(5))(N(2))] (2⋅N(2)), which features a cyclometalated hydrotris(3-p-tolylpyrazol-1-yl)borate ligand (Tp(tol')) coordinated in a κ(4)-N,N',N'',C manner, has been studied. Two methyl ethers, namely, Me(2)O...

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Valpuesta JE, Álvarez E, López-Serrano J, et al. Reversible double C-H bond activation of linear and cyclic ethers to form iridium carbenes. Chemistry. 2012;18(41):13149-59doi: 10.1002/chem.201201883.
Valpuesta, J. E., Álvarez, E., López-Serrano, J., Maya, C., & Carmona, E. (2012). Reversible double C-H bond activation of linear and cyclic ethers to form iridium carbenes. Chemistry (Weinheim an der Bergstrasse, Germany), 18(41), 13149-59. https://doi.org/10.1002/chem.201201883
Valpuesta, Jose E V, et al. "Reversible double C-H bond activation of linear and cyclic ethers to form iridium carbenes." Chemistry (Weinheim an der Bergstrasse, Germany) vol. 18,41 (2012): 13149-59. doi: https://doi.org/10.1002/chem.201201883
Valpuesta JE, Álvarez E, López-Serrano J, Maya C, Carmona E. Reversible double C-H bond activation of linear and cyclic ethers to form iridium carbenes. Chemistry. 2012 Oct 08;18(41):13149-59. doi: 10.1002/chem.201201883. Epub 2012 Sep 07. PMID: 22962021.
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Ligand-Enabled, Copper-Promoted Regio- and Chemoselective Hydroxylation of Arenes, Aryl Halides, and Aryl Methyl Ethers.

The Journal of organic chemistry

Singh BK, Jana R.
PMID: 26762789
J Org Chem. 2016 Feb 05;81(3):831-41. doi: 10.1021/acs.joc.5b02302. Epub 2016 Jan 25.

We report here a practical method for the ortho C-H hydroxylation of benzamides with inexpensive copper(II) acetate monohydrate and a pyridine ligand. An intra- and intermolecular ligand combination was explored to achieve regio- and chemoselective hydroxylation. Interestingly, typical regiochemical...

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Singh BK, Jana R. Ligand-Enabled, Copper-Promoted Regio- and Chemoselective Hydroxylation of Arenes, Aryl Halides, and Aryl Methyl Ethers. J Org Chem. 2016;81(3):831-41doi: 10.1021/acs.joc.5b02302.
Singh, B. K., & Jana, R. (2016). Ligand-Enabled, Copper-Promoted Regio- and Chemoselective Hydroxylation of Arenes, Aryl Halides, and Aryl Methyl Ethers. The Journal of organic chemistry, 81(3), 831-41. https://doi.org/10.1021/acs.joc.5b02302
Singh, Bijaya Kumar, and Jana, Ranjan. "Ligand-Enabled, Copper-Promoted Regio- and Chemoselective Hydroxylation of Arenes, Aryl Halides, and Aryl Methyl Ethers." The Journal of organic chemistry vol. 81,3 (2016): 831-41. doi: https://doi.org/10.1021/acs.joc.5b02302
Singh BK, Jana R. Ligand-Enabled, Copper-Promoted Regio- and Chemoselective Hydroxylation of Arenes, Aryl Halides, and Aryl Methyl Ethers. J Org Chem. 2016 Feb 05;81(3):831-41. doi: 10.1021/acs.joc.5b02302. Epub 2016 Jan 25. PMID: 26762789.
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Zirconocene-Mediated Selective C-C Bond Cleavage of Strained Carbocycles: Scope and Mechanism.

The Journal of organic chemistry

Bruffaerts J, Vasseur A, Singh S, Masarwa A, Didier D, Oskar L, Perrin L, Eisenstein O, Marek I.
PMID: 29537856
J Org Chem. 2018 Apr 06;83(7):3497-3515. doi: 10.1021/acs.joc.7b03115. Epub 2018 Mar 27.

Several approaches using organozirconocene species for the remote cleavage of strained three-membered ring carbocycles are described. ω-Ene polysubstituted cyclopropanes, alkylidenecyclopropanes, ω-ene spiro[2.2]pentanes, and ω-ene cyclopropyl methyl ethers were successfully transformed into stereodefined organometallic intermediates, allowing an easy access to...

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Bruffaerts J, Vasseur A, Singh S, et al. Zirconocene-Mediated Selective C-C Bond Cleavage of Strained Carbocycles: Scope and Mechanism. J Org Chem. 2018;83(7):3497-3515doi: 10.1021/acs.joc.7b03115.
Bruffaerts, J., Vasseur, A., Singh, S., Masarwa, A., Didier, D., Oskar, L., Perrin, L., Eisenstein, O., & Marek, I. (2018). Zirconocene-Mediated Selective C-C Bond Cleavage of Strained Carbocycles: Scope and Mechanism. The Journal of organic chemistry, 83(7), 3497-3515. https://doi.org/10.1021/acs.joc.7b03115
Bruffaerts, Jeffrey, et al. "Zirconocene-Mediated Selective C-C Bond Cleavage of Strained Carbocycles: Scope and Mechanism." The Journal of organic chemistry vol. 83,7 (2018): 3497-3515. doi: https://doi.org/10.1021/acs.joc.7b03115
Bruffaerts J, Vasseur A, Singh S, Masarwa A, Didier D, Oskar L, Perrin L, Eisenstein O, Marek I. Zirconocene-Mediated Selective C-C Bond Cleavage of Strained Carbocycles: Scope and Mechanism. J Org Chem. 2018 Apr 06;83(7):3497-3515. doi: 10.1021/acs.joc.7b03115. Epub 2018 Mar 27. PMID: 29537856.
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Attenuation of Ni(0) Decomposition: Mechanistic Insights into AgF-Assisted Nickel-Mediated Silylation.

Inorganic chemistry

Balakrishnan V, Murugesan V, Chindan B, Rasappan R.
PMID: 34995056
Inorg Chem. 2022 Jan 07; doi: 10.1021/acs.inorgchem.1c03108. Epub 2022 Jan 07.

In nickel-mediated Kumada cross-coupling reactions, low valent active nickel complexes are often generated in situ and the ligands usually govern the reactivity or stability of these complexes. However, the decomposition of active nickel complexes is inevitable if the subsequent...

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Balakrishnan V, Murugesan V, Chindan B, et al. Attenuation of Ni(0) Decomposition: Mechanistic Insights into AgF-Assisted Nickel-Mediated Silylation. Inorg Chem. 2022;doi: 10.1021/acs.inorgchem.1c03108.
Balakrishnan, V., Murugesan, V., Chindan, B., & Rasappan, R. (2022). Attenuation of Ni(0) Decomposition: Mechanistic Insights into AgF-Assisted Nickel-Mediated Silylation. Inorganic chemistry, . https://doi.org/10.1021/acs.inorgchem.1c03108
Balakrishnan, Venkadesh, et al. "Attenuation of Ni(0) Decomposition: Mechanistic Insights into AgF-Assisted Nickel-Mediated Silylation." Inorganic chemistry vol. (2022). doi: https://doi.org/10.1021/acs.inorgchem.1c03108
Balakrishnan V, Murugesan V, Chindan B, Rasappan R. Attenuation of Ni(0) Decomposition: Mechanistic Insights into AgF-Assisted Nickel-Mediated Silylation. Inorg Chem. 2022 Jan 07; doi: 10.1021/acs.inorgchem.1c03108. Epub 2022 Jan 07. PMID: 34995056.
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Excited Precursor Reactivity, Fast 1,2-H Shifts, and Diffusion-Controlled Methanol Insertion in 1,2-Diphenylalkylidenes.

The Journal of organic chemistry

Motschiedler K, Gudmundsdottir A, Toscano JP, Platz M, Garcia-Garibay MA.
PMID: 34237870
J Org Chem. 1999 Jul 09;64(14):5139-5147. doi: 10.1021/jo990172i.

The photochemistry of several arylalkyldiazo compounds has been investigated by steady-state direct and triplet sensitized irradiations and by nanosecond laser flash photolysis. Steady-state photolyses in methanol yielded methyl ethers and alkenes as the only significant products. Ethers were formed...

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Motschiedler K, Gudmundsdottir A, Toscano JP, et al. Excited Precursor Reactivity, Fast 1,2-H Shifts, and Diffusion-Controlled Methanol Insertion in 1,2-Diphenylalkylidenes. J Org Chem. 1999;64(14):5139-5147doi: 10.1021/jo990172i.
Motschiedler, K., Gudmundsdottir, A., Toscano, J. P., Platz, M., & Garcia-Garibay, M. A. (1999). Excited Precursor Reactivity, Fast 1,2-H Shifts, and Diffusion-Controlled Methanol Insertion in 1,2-Diphenylalkylidenes. The Journal of organic chemistry, 64(14), 5139-5147. https://doi.org/10.1021/jo990172i
Motschiedler, Krista, et al. "Excited Precursor Reactivity, Fast 1,2-H Shifts, and Diffusion-Controlled Methanol Insertion in 1,2-Diphenylalkylidenes." The Journal of organic chemistry vol. 64,14 (1999): 5139-5147. doi: https://doi.org/10.1021/jo990172i
Motschiedler K, Gudmundsdottir A, Toscano JP, Platz M, Garcia-Garibay MA. Excited Precursor Reactivity, Fast 1,2-H Shifts, and Diffusion-Controlled Methanol Insertion in 1,2-Diphenylalkylidenes. J Org Chem. 1999 Jul 09;64(14):5139-5147. doi: 10.1021/jo990172i. PMID: 34237870.
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