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Highly Enantioselective Claisen Rearrangement of Imidates Derived from Primary Allyl Alcohols.

The Journal of organic chemistry

Metz P, Hungerhoff B.
PMID: 11671772
J Org Chem. 1997 Jun 27;62(13):4442-4448. doi: 10.1021/jo970123a.

A highly enantioselective and diastereoselective Claisen rearrangement of N-arylimidates derived from an axially chiral binaphthylamine auxiliary is reported. Upon deprotonation of the imidates with lithium diethylamide, the resultant azaenolates rearrange at 0 degrees C to give anti alpha,beta-disubstituted, gamma,delta-unsaturated...

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Metz P, Hungerhoff B. Highly Enantioselective Claisen Rearrangement of Imidates Derived from Primary Allyl Alcohols. J Org Chem. 1997;62(13):4442-4448doi: 10.1021/jo970123a.
Metz, P., & Hungerhoff, B. (1997). Highly Enantioselective Claisen Rearrangement of Imidates Derived from Primary Allyl Alcohols. The Journal of organic chemistry, 62(13), 4442-4448. https://doi.org/10.1021/jo970123a
Metz, Peter, and Hungerhoff, Benno. "Highly Enantioselective Claisen Rearrangement of Imidates Derived from Primary Allyl Alcohols." The Journal of organic chemistry vol. 62,13 (1997): 4442-4448. doi: https://doi.org/10.1021/jo970123a
Metz P, Hungerhoff B. Highly Enantioselective Claisen Rearrangement of Imidates Derived from Primary Allyl Alcohols. J Org Chem. 1997 Jun 27;62(13):4442-4448. doi: 10.1021/jo970123a. PMID: 11671772.
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Inter- and intramolecular pathways for the formation of tetrahydrofurans from beta-(Phosphatoxy)alkyl radicals. Evidence for a dissociative mechanism.

The Journal of organic chemistry

Crich D, Huang X, Newcomb M.
PMID: 10813967
J Org Chem. 2000 Jan 28;65(2):523-9. doi: 10.1021/jo991570o.

beta-(Phosphatoxy)alkyl radicals generated by photolysis of Barton PTOC esters in the presence of allyl alcohol and tert-butyl mercaptan undergo nucleophilic substitution followed by 5-exo-trig radical ring closure leading to tetrahydrofurans in good yield and with high trans selectivity. beta-(Phosphatoxy)alkyl...

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Crich D, Huang X, Newcomb M. Inter- and intramolecular pathways for the formation of tetrahydrofurans from beta-(Phosphatoxy)alkyl radicals. Evidence for a dissociative mechanism. J Org Chem. 2000;65(2):523-9doi: 10.1021/jo991570o.
Crich, D., Huang, X., & Newcomb, M. (2000). Inter- and intramolecular pathways for the formation of tetrahydrofurans from beta-(Phosphatoxy)alkyl radicals. Evidence for a dissociative mechanism. The Journal of organic chemistry, 65(2), 523-9. https://doi.org/10.1021/jo991570o
Crich, et al. "Inter- and intramolecular pathways for the formation of tetrahydrofurans from beta-(Phosphatoxy)alkyl radicals. Evidence for a dissociative mechanism." The Journal of organic chemistry vol. 65,2 (2000): 523-9. doi: https://doi.org/10.1021/jo991570o
Crich D, Huang X, Newcomb M. Inter- and intramolecular pathways for the formation of tetrahydrofurans from beta-(Phosphatoxy)alkyl radicals. Evidence for a dissociative mechanism. J Org Chem. 2000 Jan 28;65(2):523-9. doi: 10.1021/jo991570o. PMID: 10813967.
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Pd-catalyzed nucleophilic alkylation of aliphatic aldehydes with allyl alcohols: allyl, 2-tetrahydrofuryl, and 2-tetrahydropyranyl ethers as useful C3, C4, and C5 sources.

Angewandte Chemie (International ed. in English)

Kimura M, Shimizu M, Shibata K, Tazoe M, Tamaru Y.
PMID: 12888967
Angew Chem Int Ed Engl. 2003 Jul 28;42(29):3392-5. doi: 10.1002/anie.200351182.

No abstract available.

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Kimura M, Shimizu M, Shibata K, et al. Pd-catalyzed nucleophilic alkylation of aliphatic aldehydes with allyl alcohols: allyl, 2-tetrahydrofuryl, and 2-tetrahydropyranyl ethers as useful C3, C4, and C5 sources. Angew Chem Int Ed Engl. 2003;42(29):3392-5doi: 10.1002/anie.200351182.
Kimura, M., Shimizu, M., Shibata, K., Tazoe, M., & Tamaru, Y. (2003). Pd-catalyzed nucleophilic alkylation of aliphatic aldehydes with allyl alcohols: allyl, 2-tetrahydrofuryl, and 2-tetrahydropyranyl ethers as useful C3, C4, and C5 sources. Angewandte Chemie (International ed. in English), 42(29), 3392-5. https://doi.org/10.1002/anie.200351182
Kimura, Masanari, et al. "Pd-catalyzed nucleophilic alkylation of aliphatic aldehydes with allyl alcohols: allyl, 2-tetrahydrofuryl, and 2-tetrahydropyranyl ethers as useful C3, C4, and C5 sources." Angewandte Chemie (International ed. in English) vol. 42,29 (2003): 3392-5. doi: https://doi.org/10.1002/anie.200351182
Kimura M, Shimizu M, Shibata K, Tazoe M, Tamaru Y. Pd-catalyzed nucleophilic alkylation of aliphatic aldehydes with allyl alcohols: allyl, 2-tetrahydrofuryl, and 2-tetrahydropyranyl ethers as useful C3, C4, and C5 sources. Angew Chem Int Ed Engl. 2003 Jul 28;42(29):3392-5. doi: 10.1002/anie.200351182. PMID: 12888967.
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Silica-Supported Tantalum Catalysts for Asymmetric Epoxidations of Allyl Alcohols.

Angewandte Chemie (International ed. in English)

Meunier D, Piechaczyk A, de Mallmann A, Basset JM.
PMID: 10602235
Angew Chem Int Ed Engl. 1999 Dec 03;38(23):3540-3542. doi: 10.1002/(sici)1521-3773(19991203)38:23<3540::aid-anie3540>3.3.co;2-l.

Tantalum good, titanium bad: This appears to be the case for silica-supported catalysts for the asymmetric epoxidation of allyl alcohols. Complexes such as [SiO-Ta(OEt)(4)] were prepared from silica and [Ta(=CHCMe(3))(CH(2)CMe(3))(3)], and in the presence of a tartrate and an...

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Meunier D, Piechaczyk A, de Mallmann A, et al. Silica-Supported Tantalum Catalysts for Asymmetric Epoxidations of Allyl Alcohols. Angew Chem Int Ed Engl. 1999;38(23):3540-3542doi: 10.1002/(sici)1521-3773(19991203)38:23<3540::aid-anie3540>3.3.co;2-l.
Meunier, D., Piechaczyk, A., de Mallmann A, & Basset, J. M. (1999). Silica-Supported Tantalum Catalysts for Asymmetric Epoxidations of Allyl Alcohols. Angewandte Chemie (International ed. in English), 38(23), 3540-3542. https://doi.org/10.1002/(sici)1521-3773(19991203)38:23<3540::aid-anie3540>3.3.co;2-l
Meunier, et al. "Silica-Supported Tantalum Catalysts for Asymmetric Epoxidations of Allyl Alcohols." Angewandte Chemie (International ed. in English) vol. 38,23 (1999): 3540-3542. doi: https://doi.org/10.1002/(sici)1521-3773(19991203)38:23<3540::aid-anie3540>3.3.co;2-l
Meunier D, Piechaczyk A, de Mallmann A, Basset JM. Silica-Supported Tantalum Catalysts for Asymmetric Epoxidations of Allyl Alcohols. Angew Chem Int Ed Engl. 1999 Dec 03;38(23):3540-3542. doi: 10.1002/(sici)1521-3773(19991203)38:23<3540::aid-anie3540>3.3.co;2-l. PMID: 10602235.
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The Change in the Properties of Sodium Dodecyl Sulfate Micelles upon Addition of Isomeric and Unsaturated Short-Chain Alcohols Probed by Photophysical Methods.

Journal of colloid and interface science

Romani AP, Gehlen MH, Quina FH.
PMID: 11446816
J Colloid Interface Sci. 2001 Aug 01;240(1):335-339. doi: 10.1006/jcis.2001.7623.

The properties of sodium dodecyl sulfate micelles (SDS) in the presence of 1-propanol, 2-propanol, and 2-propen-1-ol (allyl alcohol) were investigated using electrical conductivity and fluorescence quenching methods. The constants of association of the alcohols to SDS micelles, obtained experimentally...

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Romani AP, Gehlen MH, Quina FH. The Change in the Properties of Sodium Dodecyl Sulfate Micelles upon Addition of Isomeric and Unsaturated Short-Chain Alcohols Probed by Photophysical Methods. J Colloid Interface Sci. 2001;240(1):335-339doi: 10.1006/jcis.2001.7623.
Romani, A. P., Gehlen, M. H., & Quina, F. H. (2001). The Change in the Properties of Sodium Dodecyl Sulfate Micelles upon Addition of Isomeric and Unsaturated Short-Chain Alcohols Probed by Photophysical Methods. Journal of colloid and interface science, 240(1), 335-339. https://doi.org/10.1006/jcis.2001.7623
Romani, Ana P., et al. "The Change in the Properties of Sodium Dodecyl Sulfate Micelles upon Addition of Isomeric and Unsaturated Short-Chain Alcohols Probed by Photophysical Methods." Journal of colloid and interface science vol. 240,1 (2001): 335-339. doi: https://doi.org/10.1006/jcis.2001.7623
Romani AP, Gehlen MH, Quina FH. The Change in the Properties of Sodium Dodecyl Sulfate Micelles upon Addition of Isomeric and Unsaturated Short-Chain Alcohols Probed by Photophysical Methods. J Colloid Interface Sci. 2001 Aug 01;240(1):335-339. doi: 10.1006/jcis.2001.7623. PMID: 11446816.
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Surface Organometallic Chemistry on Oxides: Reaction of Trimethylphosphine with Bis(allyl)rhodium Grafted onto Silica.

Inorganic chemistry

Scott SL, Dufour P, Santini CC, Basset JM.
PMID: 11666259
Inorg Chem. 1996 Feb 14;35(4):869-875. doi: 10.1021/ic9405790.

The reaction of Rh(eta(3)-C(3)H(5))(3) with the surface hydroxyl groups of partially dehydroxylated silica leads to the formation of the surface organometallic complex (&tbd1;SiO)(&tbd1;SiOX)Rh(eta(3)-C(3)H(5))(2), 1 (where X is H or Si&tbd1;), with evolution of propene. The reaction of 1 with...

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Scott SL, Dufour P, Santini CC, et al. Surface Organometallic Chemistry on Oxides: Reaction of Trimethylphosphine with Bis(allyl)rhodium Grafted onto Silica. Inorg Chem. 1996;35(4):869-875doi: 10.1021/ic9405790.
Scott, S. L., Dufour, P., Santini, C. C., & Basset, J. M. (1996). Surface Organometallic Chemistry on Oxides: Reaction of Trimethylphosphine with Bis(allyl)rhodium Grafted onto Silica. Inorganic chemistry, 35(4), 869-875. https://doi.org/10.1021/ic9405790
Scott, Susannah L., et al. "Surface Organometallic Chemistry on Oxides: Reaction of Trimethylphosphine with Bis(allyl)rhodium Grafted onto Silica." Inorganic chemistry vol. 35,4 (1996): 869-875. doi: https://doi.org/10.1021/ic9405790
Scott SL, Dufour P, Santini CC, Basset JM. Surface Organometallic Chemistry on Oxides: Reaction of Trimethylphosphine with Bis(allyl)rhodium Grafted onto Silica. Inorg Chem. 1996 Feb 14;35(4):869-875. doi: 10.1021/ic9405790. PMID: 11666259.
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[3,3] Sigmatropic rearrangement of boron-containing allyl alcohols: synthesis of allyl addition reagents.

Angewandte Chemie (International ed. in English)

Pietruszka J, Schöne N.
PMID: 14639737
Angew Chem Int Ed Engl. 2003 Nov 24;42(45):5638-41. doi: 10.1002/anie.200352210.

No abstract available.

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Pietruszka J, Schöne N. [3,3] Sigmatropic rearrangement of boron-containing allyl alcohols: synthesis of allyl addition reagents. Angew Chem Int Ed Engl. 2003;42(45):5638-41doi: 10.1002/anie.200352210.
Pietruszka, J., & Schöne, N. (2003). [3,3] Sigmatropic rearrangement of boron-containing allyl alcohols: synthesis of allyl addition reagents. Angewandte Chemie (International ed. in English), 42(45), 5638-41. https://doi.org/10.1002/anie.200352210
Pietruszka, Jörg, and Schöne, Niklas. "[3,3] Sigmatropic rearrangement of boron-containing allyl alcohols: synthesis of allyl addition reagents." Angewandte Chemie (International ed. in English) vol. 42,45 (2003): 5638-41. doi: https://doi.org/10.1002/anie.200352210
Pietruszka J, Schöne N. [3,3] Sigmatropic rearrangement of boron-containing allyl alcohols: synthesis of allyl addition reagents. Angew Chem Int Ed Engl. 2003 Nov 24;42(45):5638-41. doi: 10.1002/anie.200352210. PMID: 14639737.
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Insight into the partial oxidation of propene: the reactions of 2-propen-1-ol on clean and O-covered Mo(110).

Journal of the American Chemical Society

Deiner LJ, Serafin JG, Friend CM, Weller SG, Levinson JA, Palmer RE.
PMID: 14570501
J Am Chem Soc. 2003 Oct 29;125(43):13252-7. doi: 10.1021/ja030250q.

The reactions of 2-propen-1-ol (allyl alcohol) were studied on clean and O-covered Mo(110) to understand the effect of resonance stabilization and the presence of surface oxygen on reaction selectivity. Propene is the only gaseous hydrocarbon product evolved from allyl...

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Deiner LJ, Serafin JG, Friend CM, et al. Insight into the partial oxidation of propene: the reactions of 2-propen-1-ol on clean and O-covered Mo(110). J Am Chem Soc. 2003;125(43):13252-7doi: 10.1021/ja030250q.
Deiner, L. J., Serafin, J. G., Friend, C. M., Weller, S. G., Levinson, J. A., & Palmer, R. E. (2003). Insight into the partial oxidation of propene: the reactions of 2-propen-1-ol on clean and O-covered Mo(110). Journal of the American Chemical Society, 125(43), 13252-7. https://doi.org/10.1021/ja030250q
Deiner, L J, et al. "Insight into the partial oxidation of propene: the reactions of 2-propen-1-ol on clean and O-covered Mo(110)." Journal of the American Chemical Society vol. 125,43 (2003): 13252-7. doi: https://doi.org/10.1021/ja030250q
Deiner LJ, Serafin JG, Friend CM, Weller SG, Levinson JA, Palmer RE. Insight into the partial oxidation of propene: the reactions of 2-propen-1-ol on clean and O-covered Mo(110). J Am Chem Soc. 2003 Oct 29;125(43):13252-7. doi: 10.1021/ja030250q. PMID: 14570501.
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Cooperative Friedel-Crafts catalysis in heterobimetallic regime: alkylation of aromatics by pi-activated alcohols.

Journal of the American Chemical Society

Choudhury J, Podder S, Roy S.
PMID: 15853308
J Am Chem Soc. 2005 May 04;127(17):6162-3. doi: 10.1021/ja0506004.

The highly active Friedel-Crafts alkylation (FCA) catalyst, [Ir(COD)Cl(SnCl3)(SnCl4)(arene)]+Cl- (1-SnCl4), is easily generated in one-pot from [Ir(COD)Cl]2 or [Ir(COD)(mu-Cl)Cl(SnCl3)]2 (1) and SnCl4. The reaction of arenes, heteroarenes with benzyl, and allyl alcohols is promoted by 1-SnCl4 (1 mol %) with...

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Choudhury J, Podder S, Roy S. Cooperative Friedel-Crafts catalysis in heterobimetallic regime: alkylation of aromatics by pi-activated alcohols. J Am Chem Soc. 2005;127(17):6162-3doi: 10.1021/ja0506004.
Choudhury, J., Podder, S., & Roy, S. (2005). Cooperative Friedel-Crafts catalysis in heterobimetallic regime: alkylation of aromatics by pi-activated alcohols. Journal of the American Chemical Society, 127(17), 6162-3. https://doi.org/10.1021/ja0506004
Choudhury, Joyanta, et al. "Cooperative Friedel-Crafts catalysis in heterobimetallic regime: alkylation of aromatics by pi-activated alcohols." Journal of the American Chemical Society vol. 127,17 (2005): 6162-3. doi: https://doi.org/10.1021/ja0506004
Choudhury J, Podder S, Roy S. Cooperative Friedel-Crafts catalysis in heterobimetallic regime: alkylation of aromatics by pi-activated alcohols. J Am Chem Soc. 2005 May 04;127(17):6162-3. doi: 10.1021/ja0506004. PMID: 15853308.
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Allyl Alcohol Selection for Lower Alcohol Dehydrogenase Activity in Nicotiana plumbaginifolia Cultured Cells.

Plant physiology

Widholm JM, Kishinami I.
PMID: 16665878
Plant Physiol. 1988 Jan;86(1):266-9. doi: 10.1104/pp.86.1.266.

One cell strain with stable tolerance to allyl alcohol (AA(r)) was selected from 6 x 10(8) suspension cultured Nicotiana plumbaginifolia Viviani cells. The selected strain contained one-half the alcohol dehydrogenase (ADH) activity of the wild type (NP) due to...

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Widholm JM, Kishinami I. Allyl Alcohol Selection for Lower Alcohol Dehydrogenase Activity in Nicotiana plumbaginifolia Cultured Cells. Plant Physiol. 1988;86(1):266-9doi: 10.1104/pp.86.1.266.
Widholm, J. M., & Kishinami, I. (1988). Allyl Alcohol Selection for Lower Alcohol Dehydrogenase Activity in Nicotiana plumbaginifolia Cultured Cells. Plant physiology, 86(1), 266-9. https://doi.org/10.1104/pp.86.1.266
Widholm, J M, and Kishinami, I. "Allyl Alcohol Selection for Lower Alcohol Dehydrogenase Activity in Nicotiana plumbaginifolia Cultured Cells." Plant physiology vol. 86,1 (1988): 266-9. doi: https://doi.org/10.1104/pp.86.1.266
Widholm JM, Kishinami I. Allyl Alcohol Selection for Lower Alcohol Dehydrogenase Activity in Nicotiana plumbaginifolia Cultured Cells. Plant Physiol. 1988 Jan;86(1):266-9. doi: 10.1104/pp.86.1.266. PMID: 16665878; PMCID: PMC1054465.
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Palladium-catalyzed, carboxylic acid-assisted allylic substitution of carbon nucleophiles with allyl alcohols as allylating agents in water.

Organic letters

Manabe K, Kobayashi S.
PMID: 12943397
Org Lett. 2003 Sep 04;5(18):3241-4. doi: 10.1021/ol035126q.

[structure: see text] Allylic substitution of allyl alcohols in water as a suspension medium has been realized using a combination of tetrakis(triphenylphosphine)palladium and a carboxylic acid such as 1-adamantanecarboxylic acid. Various substrates turned out to be applicable to this...

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Manabe K, Kobayashi S. Palladium-catalyzed, carboxylic acid-assisted allylic substitution of carbon nucleophiles with allyl alcohols as allylating agents in water. Org Lett. 2003;5(18):3241-4doi: 10.1021/ol035126q.
Manabe, K., & Kobayashi, S. (2003). Palladium-catalyzed, carboxylic acid-assisted allylic substitution of carbon nucleophiles with allyl alcohols as allylating agents in water. Organic letters, 5(18), 3241-4. https://doi.org/10.1021/ol035126q
Manabe, Kei, and Kobayashi, Shū. "Palladium-catalyzed, carboxylic acid-assisted allylic substitution of carbon nucleophiles with allyl alcohols as allylating agents in water." Organic letters vol. 5,18 (2003): 3241-4. doi: https://doi.org/10.1021/ol035126q
Manabe K, Kobayashi S. Palladium-catalyzed, carboxylic acid-assisted allylic substitution of carbon nucleophiles with allyl alcohols as allylating agents in water. Org Lett. 2003 Sep 04;5(18):3241-4. doi: 10.1021/ol035126q. PMID: 12943397.
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Functionalized chiral vinyl aminosulfoxonium salts: asymmetric synthesis and application to the synthesis of enantiopure unsaturated prolines, beta,gamma-dehydro amino acids, and cyclopentanoid keto aminosulfoxonium ylides.

Journal of the American Chemical Society

Tiwari SK, Gais HJ, Lindenmaier A, Babu GS, Raabe G, Reddy LR, Köhler F, Günter M, Koep S, Iska VB.
PMID: 16734492
J Am Chem Soc. 2006 Jun 07;128(22):7360-73. doi: 10.1021/ja061152i.

Methylation of the enantiopure functionalized vinyl sulfoximines 5a-e and 14a-d followed by a F- ion or DBU-mediated isomerization of the vinyl aminosulfoxonium salts 7a-e and 15a-d, respectively, gave the allyl aminosulfoxonium salts 10a-e and 17a-d, respectively. A concomitant intramolecular...

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Tiwari SK, Gais HJ, Lindenmaier A, et al. Functionalized chiral vinyl aminosulfoxonium salts: asymmetric synthesis and application to the synthesis of enantiopure unsaturated prolines, beta,gamma-dehydro amino acids, and cyclopentanoid keto aminosulfoxonium ylides. J Am Chem Soc. 2006;128(22):7360-73doi: 10.1021/ja061152i.
Tiwari, S. K., Gais, H. J., Lindenmaier, A., Babu, G. S., Raabe, G., Reddy, L. R., Köhler, F., Günter, M., Koep, S., & Iska, V. B. (2006). Functionalized chiral vinyl aminosulfoxonium salts: asymmetric synthesis and application to the synthesis of enantiopure unsaturated prolines, beta,gamma-dehydro amino acids, and cyclopentanoid keto aminosulfoxonium ylides. Journal of the American Chemical Society, 128(22), 7360-73. https://doi.org/10.1021/ja061152i
Tiwari, Shashi Kant, et al. "Functionalized chiral vinyl aminosulfoxonium salts: asymmetric synthesis and application to the synthesis of enantiopure unsaturated prolines, beta,gamma-dehydro amino acids, and cyclopentanoid keto aminosulfoxonium ylides." Journal of the American Chemical Society vol. 128,22 (2006): 7360-73. doi: https://doi.org/10.1021/ja061152i
Tiwari SK, Gais HJ, Lindenmaier A, Babu GS, Raabe G, Reddy LR, Köhler F, Günter M, Koep S, Iska VB. Functionalized chiral vinyl aminosulfoxonium salts: asymmetric synthesis and application to the synthesis of enantiopure unsaturated prolines, beta,gamma-dehydro amino acids, and cyclopentanoid keto aminosulfoxonium ylides. J Am Chem Soc. 2006 Jun 07;128(22):7360-73. doi: 10.1021/ja061152i. PMID: 16734492.
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Showing 13 to 24 of 257 entries