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Copper(I) Complexes of Zwitterionic Imidazolium-2-Amidinates, a Promising Class of Electroneutral, Amidinate-Type Ligands.

Inorganic chemistry

Márquez A, Ávila E, Urbaneja C, Álvarez E, Palma P, Cámpora J.
PMID: 26517572
Inorg Chem. 2015 Nov 16;54(22):11007-17. doi: 10.1021/acs.inorgchem.5b02141. Epub 2015 Oct 30.

The first complexes containing imidazolium-2-amidinates as ligands (betaine-type adducts of imidazolium-based carbenes and carbodiimides, NHC-CDI) are reported. Interaction of the sterically hindered betaines ICyCDI(DiPP) and IMeCDI(DiPP) [both bearing 2,6-diisopropylphenyl (DiPP) substituents on the terminal N atoms] with Cu(I) acetate...

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Márquez A, Ávila E, Urbaneja C, et al. Copper(I) Complexes of Zwitterionic Imidazolium-2-Amidinates, a Promising Class of Electroneutral, Amidinate-Type Ligands. Inorg Chem. 2015;54(22):11007-17doi: 10.1021/acs.inorgchem.5b02141.
Márquez, A., Ávila, E., Urbaneja, C., Álvarez, E., Palma, P., & Cámpora, J. (2015). Copper(I) Complexes of Zwitterionic Imidazolium-2-Amidinates, a Promising Class of Electroneutral, Amidinate-Type Ligands. Inorganic chemistry, 54(22), 11007-17. https://doi.org/10.1021/acs.inorgchem.5b02141
Márquez, Astrid, et al. "Copper(I) Complexes of Zwitterionic Imidazolium-2-Amidinates, a Promising Class of Electroneutral, Amidinate-Type Ligands." Inorganic chemistry vol. 54,22 (2015): 11007-17. doi: https://doi.org/10.1021/acs.inorgchem.5b02141
Márquez A, Ávila E, Urbaneja C, Álvarez E, Palma P, Cámpora J. Copper(I) Complexes of Zwitterionic Imidazolium-2-Amidinates, a Promising Class of Electroneutral, Amidinate-Type Ligands. Inorg Chem. 2015 Nov 16;54(22):11007-17. doi: 10.1021/acs.inorgchem.5b02141. Epub 2015 Oct 30. PMID: 26517572.
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Catalytic hydroacetylenation of carbodiimides with homoleptic alkaline earth hexamethyldisilazides.

Dalton transactions (Cambridge, England : 2003)

Arrowsmith M, Crimmin MR, Hill MS, Lomas SL, Heng MS, Hitchcock PB, Kociok-Köhn G.
PMID: 24434957
Dalton Trans. 2014 Oct 14;43(38):14249-56. doi: 10.1039/c3dt53542h.

The homoleptic alkaline earth hexamethyldisilazides, [M{N(SiMe3)2}2(THF)2] (M = Mg 1a; Ca 1b; Sr 1c), have been shown to act as efficient precatalysts for the hydroacetylenation of organic carbodiimides with alkyl- and arylacetylenes. Catalytic activity was observed to increase with...

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Arrowsmith M, Crimmin MR, Hill MS, et al. Catalytic hydroacetylenation of carbodiimides with homoleptic alkaline earth hexamethyldisilazides. Dalton Trans. 2014;43(38):14249-56doi: 10.1039/c3dt53542h.
Arrowsmith, M., Crimmin, M. R., Hill, M. S., Lomas, S. L., Heng, M. S., Hitchcock, P. B., & Kociok-Köhn, G. (2014). Catalytic hydroacetylenation of carbodiimides with homoleptic alkaline earth hexamethyldisilazides. Dalton transactions (Cambridge, England : 2003), 43(38), 14249-56. https://doi.org/10.1039/c3dt53542h
Arrowsmith, Merle, et al. "Catalytic hydroacetylenation of carbodiimides with homoleptic alkaline earth hexamethyldisilazides." Dalton transactions (Cambridge, England : 2003) vol. 43,38 (2014): 14249-56. doi: https://doi.org/10.1039/c3dt53542h
Arrowsmith M, Crimmin MR, Hill MS, Lomas SL, Heng MS, Hitchcock PB, Kociok-Köhn G. Catalytic hydroacetylenation of carbodiimides with homoleptic alkaline earth hexamethyldisilazides. Dalton Trans. 2014 Oct 14;43(38):14249-56. doi: 10.1039/c3dt53542h. PMID: 24434957.
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Hydroalumination of Ketenimines and Subsequent Reactions with Heterocumulenes: Synthesis of Unsaturated Amide Derivatives and 1,3-Diimines.

The Journal of organic chemistry

Jin X, Willeke M, Lucchesi R, Daniliuc CG, Fröhlich R, Wibbeling B, Uhl W, Würthwein EU.
PMID: 26031425
J Org Chem. 2015 Jun 19;80(12):6062-75. doi: 10.1021/acs.joc.5b00466. Epub 2015 Jun 02.

The series of differently substituted ketenimines 1 was hydroluminated using di-iso-butyl aluminum hydride. For the sterically congested ketenimine 1a, preferred hydroalumination of the C═N-bond was proven by X-ray crystallography (compound 5a). In situ treatment of the hydroaluminated ketenimines 5...

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Jin X, Willeke M, Lucchesi R, et al. Hydroalumination of Ketenimines and Subsequent Reactions with Heterocumulenes: Synthesis of Unsaturated Amide Derivatives and 1,3-Diimines. J Org Chem. 2015;80(12):6062-75doi: 10.1021/acs.joc.5b00466.
Jin, X., Willeke, M., Lucchesi, R., Daniliuc, C. G., Fröhlich, R., Wibbeling, B., Uhl, W., & Würthwein, E. U. (2015). Hydroalumination of Ketenimines and Subsequent Reactions with Heterocumulenes: Synthesis of Unsaturated Amide Derivatives and 1,3-Diimines. The Journal of organic chemistry, 80(12), 6062-75. https://doi.org/10.1021/acs.joc.5b00466
Jin, Xing, et al. "Hydroalumination of Ketenimines and Subsequent Reactions with Heterocumulenes: Synthesis of Unsaturated Amide Derivatives and 1,3-Diimines." The Journal of organic chemistry vol. 80,12 (2015): 6062-75. doi: https://doi.org/10.1021/acs.joc.5b00466
Jin X, Willeke M, Lucchesi R, Daniliuc CG, Fröhlich R, Wibbeling B, Uhl W, Würthwein EU. Hydroalumination of Ketenimines and Subsequent Reactions with Heterocumulenes: Synthesis of Unsaturated Amide Derivatives and 1,3-Diimines. J Org Chem. 2015 Jun 19;80(12):6062-75. doi: 10.1021/acs.joc.5b00466. Epub 2015 Jun 02. PMID: 26031425.
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Stimuli-Responsive Frustrated Lewis-Pair-Type Reactivity of a Tungsten Iminoazaphosphiridine Complex.

Chemistry (Weinheim an der Bergstrasse, Germany)

Villalba Franco JM, Schnakenburg G, Sasamori T, Espinosa Ferao A, Streubel R.
PMID: 26031623
Chemistry. 2015 Jun 26;21(27):9650-5. doi: 10.1002/chem.201501628. Epub 2015 Jun 01.

Reactions of 3-imino-azaphosphiridine complexes 1 a,b with carbodiimides 2 a,b, isocyanates 3 a,b, and carbon dioxide are described. Whereas exchange of the carbodiimide unit occurs in the first case, an overall ring expansion takes place with phenyl isocyanate (3...

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Villalba Franco JM, Schnakenburg G, Sasamori T, et al. Stimuli-Responsive Frustrated Lewis-Pair-Type Reactivity of a Tungsten Iminoazaphosphiridine Complex. Chemistry. 2015;21(27):9650-5doi: 10.1002/chem.201501628.
Villalba Franco, J. M., Schnakenburg, G., Sasamori, T., Espinosa Ferao, A., & Streubel, R. (2015). Stimuli-Responsive Frustrated Lewis-Pair-Type Reactivity of a Tungsten Iminoazaphosphiridine Complex. Chemistry (Weinheim an der Bergstrasse, Germany), 21(27), 9650-5. https://doi.org/10.1002/chem.201501628
Villalba Franco, José Manuel, et al. "Stimuli-Responsive Frustrated Lewis-Pair-Type Reactivity of a Tungsten Iminoazaphosphiridine Complex." Chemistry (Weinheim an der Bergstrasse, Germany) vol. 21,27 (2015): 9650-5. doi: https://doi.org/10.1002/chem.201501628
Villalba Franco JM, Schnakenburg G, Sasamori T, Espinosa Ferao A, Streubel R. Stimuli-Responsive Frustrated Lewis-Pair-Type Reactivity of a Tungsten Iminoazaphosphiridine Complex. Chemistry. 2015 Jun 26;21(27):9650-5. doi: 10.1002/chem.201501628. Epub 2015 Jun 01. PMID: 26031623.
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Synthesis of carbodiimides by I2/CHP-mediated cross-coupling reaction of isocyanides with amines under metal-free conditions.

Organic letters

Zhu TH, Wang SY, Tao YQ, Ji SJ.
PMID: 25826468
Org Lett. 2015 Apr 17;17(8):1974-7. doi: 10.1021/acs.orglett.5b00722. Epub 2015 Mar 31.

An I2/CHP-mediated cross-coupling reaction of isocyanides with readily accessible amines via C-N formation is described for carbodiimide synthesis in moderate to excellent yields. This represents a metal-free strategy for a coupling reaction of isocyanides with amines, and it provides...

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Zhu TH, Wang SY, Tao YQ, et al. Synthesis of carbodiimides by I2/CHP-mediated cross-coupling reaction of isocyanides with amines under metal-free conditions. Org Lett. 2015;17(8):1974-7doi: 10.1021/acs.orglett.5b00722.
Zhu, T. H., Wang, S. Y., Tao, Y. Q., & Ji, S. J. (2015). Synthesis of carbodiimides by I2/CHP-mediated cross-coupling reaction of isocyanides with amines under metal-free conditions. Organic letters, 17(8), 1974-7. https://doi.org/10.1021/acs.orglett.5b00722
Zhu, Tong-Hao, et al. "Synthesis of carbodiimides by I2/CHP-mediated cross-coupling reaction of isocyanides with amines under metal-free conditions." Organic letters vol. 17,8 (2015): 1974-7. doi: https://doi.org/10.1021/acs.orglett.5b00722
Zhu TH, Wang SY, Tao YQ, Ji SJ. Synthesis of carbodiimides by I2/CHP-mediated cross-coupling reaction of isocyanides with amines under metal-free conditions. Org Lett. 2015 Apr 17;17(8):1974-7. doi: 10.1021/acs.orglett.5b00722. Epub 2015 Mar 31. PMID: 25826468.
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Reaction of tungsten-phosphinidene and -arsinidene complexes with carbodiimides and alkyl azides: a straightforward way to four-membered heterocycles.

Angewandte Chemie (International ed. in English)

Seidl M, Kuntz C, Bodensteiner M, Timoshkin AY, Scheer M.
PMID: 25565087
Angew Chem Int Ed Engl. 2015 Feb 23;54(9):2771-5. doi: 10.1002/anie.201410191. Epub 2015 Jan 07.

The reaction of the phosphinidene and arsinidene complexes [Cp*E{W(CO)5 }2 ] (E=P (1 a), As (1 b); Cp*=C5 Me5 ) with carbodiimides leads to the new four-membered heterocycles of the type [Cp*C(NR)2 E{W(CO)5 }2 ] (E=P: R=iPr (2 a),...

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Seidl M, Kuntz C, Bodensteiner M, et al. Reaction of tungsten-phosphinidene and -arsinidene complexes with carbodiimides and alkyl azides: a straightforward way to four-membered heterocycles. Angew Chem Int Ed Engl. 2015;54(9):2771-5doi: 10.1002/anie.201410191.
Seidl, M., Kuntz, C., Bodensteiner, M., Timoshkin, A. Y., & Scheer, M. (2015). Reaction of tungsten-phosphinidene and -arsinidene complexes with carbodiimides and alkyl azides: a straightforward way to four-membered heterocycles. Angewandte Chemie (International ed. in English), 54(9), 2771-5. https://doi.org/10.1002/anie.201410191
Seidl, Michael, et al. "Reaction of tungsten-phosphinidene and -arsinidene complexes with carbodiimides and alkyl azides: a straightforward way to four-membered heterocycles." Angewandte Chemie (International ed. in English) vol. 54,9 (2015): 2771-5. doi: https://doi.org/10.1002/anie.201410191
Seidl M, Kuntz C, Bodensteiner M, Timoshkin AY, Scheer M. Reaction of tungsten-phosphinidene and -arsinidene complexes with carbodiimides and alkyl azides: a straightforward way to four-membered heterocycles. Angew Chem Int Ed Engl. 2015 Feb 23;54(9):2771-5. doi: 10.1002/anie.201410191. Epub 2015 Jan 07. PMID: 25565087.
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Palladium-catalyzed cyclocarbonylation of o-iodoanilines with heterocumulenes: regioselective preparation of 4(3H)-quinazolinone derivatives.

The Journal of organic chemistry

Larksarp C, Alper H.
PMID: 10808454
J Org Chem. 2000 May 09;65(9):2773-7. doi: 10.1021/jo991922r.

A catalyst system comprising palladium acetate-bidentate phosphine is effective for the cyclocarbonylation of o-iodoanilines with heterocumulenes at 70-100 degrees C for 12-24 h to give the corresponding 4(3H)-quinazolinone derivatives in good yields. Utilizing o-iodoaniline with isocyanates, carbodiimides, and ketenimines...

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Larksarp C, Alper H. Palladium-catalyzed cyclocarbonylation of o-iodoanilines with heterocumulenes: regioselective preparation of 4(3H)-quinazolinone derivatives. J Org Chem. 2000;65(9):2773-7doi: 10.1021/jo991922r.
Larksarp, C., & Alper, H. (2000). Palladium-catalyzed cyclocarbonylation of o-iodoanilines with heterocumulenes: regioselective preparation of 4(3H)-quinazolinone derivatives. The Journal of organic chemistry, 65(9), 2773-7. https://doi.org/10.1021/jo991922r
Larksarp, and Alper. "Palladium-catalyzed cyclocarbonylation of o-iodoanilines with heterocumulenes: regioselective preparation of 4(3H)-quinazolinone derivatives." The Journal of organic chemistry vol. 65,9 (2000): 2773-7. doi: https://doi.org/10.1021/jo991922r
Larksarp C, Alper H. Palladium-catalyzed cyclocarbonylation of o-iodoanilines with heterocumulenes: regioselective preparation of 4(3H)-quinazolinone derivatives. J Org Chem. 2000 May 09;65(9):2773-7. doi: 10.1021/jo991922r. PMID: 10808454.
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Carbene and nitrene rearrangements: a theoretical study of cyclic allenes and carbenes, carbodiimides, and azirines.

The Journal of organic chemistry

Kuhn A, Vosswinkel M, Wentrup C.
PMID: 12467425
J Org Chem. 2002 Dec 13;67(25):9023-30. doi: 10.1021/jo0258756.

B3LYP/6-31G(d) calculations of structures, energies, and infrared spectra of several rearrangement products of (hetero)aromatic nitrenes and carbenes are reported. 3-Isoquinolylnitrene 36 ring closes to the azirine 37 prior to ring expansion to the potentially stable but unobserved seven-membered-ring carbodiimide...

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Kuhn A, Vosswinkel M, Wentrup C. Carbene and nitrene rearrangements: a theoretical study of cyclic allenes and carbenes, carbodiimides, and azirines. J Org Chem. 2002;67(25):9023-30doi: 10.1021/jo0258756.
Kuhn, A., Vosswinkel, M., & Wentrup, C. (2002). Carbene and nitrene rearrangements: a theoretical study of cyclic allenes and carbenes, carbodiimides, and azirines. The Journal of organic chemistry, 67(25), 9023-30. https://doi.org/10.1021/jo0258756
Kuhn, Arvid, et al. "Carbene and nitrene rearrangements: a theoretical study of cyclic allenes and carbenes, carbodiimides, and azirines." The Journal of organic chemistry vol. 67,25 (2002): 9023-30. doi: https://doi.org/10.1021/jo0258756
Kuhn A, Vosswinkel M, Wentrup C. Carbene and nitrene rearrangements: a theoretical study of cyclic allenes and carbenes, carbodiimides, and azirines. J Org Chem. 2002 Dec 13;67(25):9023-30. doi: 10.1021/jo0258756. PMID: 12467425.
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Reactivity of carboxyl groups in modified proteins.

FEBS letters

Frater R.
PMID: 11945573
FEBS Lett. 1971 Jan 25;12(4):186-188. doi: 10.1016/0014-5793(71)80016-9.

The reactivities of carboxyl groups to carbodiimides in non-reduced, S-carboxymethyl, and S-cyanoethyl proteins have been compared. When disulphide bonds are split, a decrease in reactivity was found, relatively minor in the S-carboxymethyl derivative and almost complete loss of reactivities...

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Frater R. Reactivity of carboxyl groups in modified proteins. FEBS Lett. 1971;12(4):186-188doi: 10.1016/0014-5793(71)80016-9.
Frater, R. (1971). Reactivity of carboxyl groups in modified proteins. FEBS letters, 12(4), 186-188. https://doi.org/10.1016/0014-5793(71)80016-9
Frater, R. "Reactivity of carboxyl groups in modified proteins." FEBS letters vol. 12,4 (1971): 186-188. doi: https://doi.org/10.1016/0014-5793(71)80016-9
Frater R. Reactivity of carboxyl groups in modified proteins. FEBS Lett. 1971 Jan 25;12(4):186-188. doi: 10.1016/0014-5793(71)80016-9. PMID: 11945573.
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Heterocumulene metathesis by iridium guanidinate and ureylene complexes: catalysis involving reversible insertion to form six-membered metallacycles.

Journal of the American Chemical Society

Holland AW, Bergman RG.
PMID: 12148979
J Am Chem Soc. 2002 Aug 07;124(31):9010-1. doi: 10.1021/ja026178y.

The four-membered metallacycles Cp*Ir((NAr)2C=Z) have been prepared for Z = NAr and Z = O. These complexes undergo facile exchange with free heterocumulenes. This exchange process can be employed to effect the rapid, catalytic metathesis of aryl carbodiimides at...

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Holland AW, Bergman RG. Heterocumulene metathesis by iridium guanidinate and ureylene complexes: catalysis involving reversible insertion to form six-membered metallacycles. J Am Chem Soc. 2002;124(31):9010-1doi: 10.1021/ja026178y.
Holland, A. W., & Bergman, R. G. (2002). Heterocumulene metathesis by iridium guanidinate and ureylene complexes: catalysis involving reversible insertion to form six-membered metallacycles. Journal of the American Chemical Society, 124(31), 9010-1. https://doi.org/10.1021/ja026178y
Holland, Andrew W, and Bergman, Robert G. "Heterocumulene metathesis by iridium guanidinate and ureylene complexes: catalysis involving reversible insertion to form six-membered metallacycles." Journal of the American Chemical Society vol. 124,31 (2002): 9010-1. doi: https://doi.org/10.1021/ja026178y
Holland AW, Bergman RG. Heterocumulene metathesis by iridium guanidinate and ureylene complexes: catalysis involving reversible insertion to form six-membered metallacycles. J Am Chem Soc. 2002 Aug 07;124(31):9010-1. doi: 10.1021/ja026178y. PMID: 12148979.
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1,4- and 1,3-dipolar reactivity of alpha-alkoxycarbonylcycloimmonium N-aminides with dipolarophiles: synthesis of new imidazo[2,1-f][1,2,4]triazinium inner salts.

The Journal of organic chemistry

Valenciano J, Sánchez-Pavón E, Cuadro AM, Vaquero JJ, Alvarez-Builla J.
PMID: 11735534
J Org Chem. 2001 Dec 14;66(25):8528-36. doi: 10.1021/jo015983c.

2-Alkoxycarbonylazolium N-aminides are interesting species, as they have the potential to act as efficient 1,4-dipole equivalents when they react with heterocumulenes, such as iso(thio)cyanates and carbodiimides. These reactions give heterobetaines containing the imidazo[2,1-f][1,2,4]triazinium system, in a formal [4 +...

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Valenciano J, Sánchez-Pavón E, Cuadro AM, et al. 1,4- and 1,3-dipolar reactivity of alpha-alkoxycarbonylcycloimmonium N-aminides with dipolarophiles: synthesis of new imidazo[2,1-f][1,2,4]triazinium inner salts. J Org Chem. 2001;66(25):8528-36doi: 10.1021/jo015983c.
Valenciano, J., Sánchez-Pavón, E., Cuadro, A. M., Vaquero, J. J., & Alvarez-Builla, J. (2001). 1,4- and 1,3-dipolar reactivity of alpha-alkoxycarbonylcycloimmonium N-aminides with dipolarophiles: synthesis of new imidazo[2,1-f][1,2,4]triazinium inner salts. The Journal of organic chemistry, 66(25), 8528-36. https://doi.org/10.1021/jo015983c
Valenciano, J, et al. "1,4- and 1,3-dipolar reactivity of alpha-alkoxycarbonylcycloimmonium N-aminides with dipolarophiles: synthesis of new imidazo[2,1-f][1,2,4]triazinium inner salts." The Journal of organic chemistry vol. 66,25 (2001): 8528-36. doi: https://doi.org/10.1021/jo015983c
Valenciano J, Sánchez-Pavón E, Cuadro AM, Vaquero JJ, Alvarez-Builla J. 1,4- and 1,3-dipolar reactivity of alpha-alkoxycarbonylcycloimmonium N-aminides with dipolarophiles: synthesis of new imidazo[2,1-f][1,2,4]triazinium inner salts. J Org Chem. 2001 Dec 14;66(25):8528-36. doi: 10.1021/jo015983c. PMID: 11735534.
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Cascade cyclizations via N,4-didehydro-2-(phenylamino)pyridine biradicals/zwitterions generated from enyne-carbodiimides.

The Journal of organic chemistry

Li H, Petersen JL, Wang KK.
PMID: 12839441
J Org Chem. 2003 Jul 11;68(14):5512-8. doi: 10.1021/jo020760n.

Thermolysis of the enyne-carbodiimides 7 having the central carbon-carbon double bond incorporated as part of the cyclopentene ring favors the formation of the corresponding N,4-didehydro-2-(phenylamino)pyridine intermediates, either as the sigma,pi-biradicals 8 or as the zwitterions 8', for subsequent synthetic...

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Li H, Petersen JL, Wang KK. Cascade cyclizations via N,4-didehydro-2-(phenylamino)pyridine biradicals/zwitterions generated from enyne-carbodiimides. J Org Chem. 2003;68(14):5512-8doi: 10.1021/jo020760n.
Li, H., Petersen, J. L., & Wang, K. K. (2003). Cascade cyclizations via N,4-didehydro-2-(phenylamino)pyridine biradicals/zwitterions generated from enyne-carbodiimides. The Journal of organic chemistry, 68(14), 5512-8. https://doi.org/10.1021/jo020760n
Li, Hongbin, et al. "Cascade cyclizations via N,4-didehydro-2-(phenylamino)pyridine biradicals/zwitterions generated from enyne-carbodiimides." The Journal of organic chemistry vol. 68,14 (2003): 5512-8. doi: https://doi.org/10.1021/jo020760n
Li H, Petersen JL, Wang KK. Cascade cyclizations via N,4-didehydro-2-(phenylamino)pyridine biradicals/zwitterions generated from enyne-carbodiimides. J Org Chem. 2003 Jul 11;68(14):5512-8. doi: 10.1021/jo020760n. PMID: 12839441.
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