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Tandem Insertion/[3,3]-Sigmatropic Rearrangement Involving the Formation of Silyl Ketene Acetals by Insertion of Rhodium Carbenes into S-Si Bonds.

Organic letters

Combs JR, Lai YC, Van Vranken DL.
PMID: 33792331
Org Lett. 2021 Apr 16;23(8):2841-2845. doi: 10.1021/acs.orglett.1c00229. Epub 2021 Apr 01.

Allyl 2-diazo-2-phenylacetates are shown to react with trimethylsilyl thioethers in the presence of rhodium(II) catalysts to generate α-allyl-α-thio silyl esters. The transformation involves a tandem process involving formal rhodium-catalyzed insertion of the carbene group into the S-Si bond to...

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Combs JR, Lai YC, Van Vranken DL. Tandem Insertion/[3,3]-Sigmatropic Rearrangement Involving the Formation of Silyl Ketene Acetals by Insertion of Rhodium Carbenes into S-Si Bonds. Org Lett. 2021;23(8):2841-2845doi: 10.1021/acs.orglett.1c00229.
Combs, J. R., Lai, Y. C., & Van Vranken, D. L. (2021). Tandem Insertion/[3,3]-Sigmatropic Rearrangement Involving the Formation of Silyl Ketene Acetals by Insertion of Rhodium Carbenes into S-Si Bonds. Organic letters, 23(8), 2841-2845. https://doi.org/10.1021/acs.orglett.1c00229
Combs, Jason R, et al. "Tandem Insertion/[3,3]-Sigmatropic Rearrangement Involving the Formation of Silyl Ketene Acetals by Insertion of Rhodium Carbenes into S-Si Bonds." Organic letters vol. 23,8 (2021): 2841-2845. doi: https://doi.org/10.1021/acs.orglett.1c00229
Combs JR, Lai YC, Van Vranken DL. Tandem Insertion/[3,3]-Sigmatropic Rearrangement Involving the Formation of Silyl Ketene Acetals by Insertion of Rhodium Carbenes into S-Si Bonds. Org Lett. 2021 Apr 16;23(8):2841-2845. doi: 10.1021/acs.orglett.1c00229. Epub 2021 Apr 01. PMID: 33792331.
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Elimination reactions of aryl phenylacetates promoted by R(2)NH/R(2)NH(2)(+) in 70 mol MeCN(aq). Effect Of the beta-phenyl group on the ketene-forming transition state.

The Journal of organic chemistry

Cho BR, Kim YK, Seung YJ, Kim JC, Pyun SY.
PMID: 10814082
J Org Chem. 2000 Feb 25;65(4):1239-42. doi: 10.1021/jo991473v.

No abstract available.

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Cho BR, Kim YK, Seung YJ, et al. Elimination reactions of aryl phenylacetates promoted by R(2)NH/R(2)NH(2)(+) in 70 mol MeCN(aq). Effect Of the beta-phenyl group on the ketene-forming transition state. J Org Chem. 2000;65(4):1239-42doi: 10.1021/jo991473v.
Cho, B. R., Kim, Y. K., Seung, Y. J., Kim, J. C., & Pyun, S. Y. (2000). Elimination reactions of aryl phenylacetates promoted by R(2)NH/R(2)NH(2)(+) in 70 mol MeCN(aq). Effect Of the beta-phenyl group on the ketene-forming transition state. The Journal of organic chemistry, 65(4), 1239-42. https://doi.org/10.1021/jo991473v
Cho, et al. "Elimination reactions of aryl phenylacetates promoted by R(2)NH/R(2)NH(2)(+) in 70 mol MeCN(aq). Effect Of the beta-phenyl group on the ketene-forming transition state." The Journal of organic chemistry vol. 65,4 (2000): 1239-42. doi: https://doi.org/10.1021/jo991473v
Cho BR, Kim YK, Seung YJ, Kim JC, Pyun SY. Elimination reactions of aryl phenylacetates promoted by R(2)NH/R(2)NH(2)(+) in 70 mol MeCN(aq). Effect Of the beta-phenyl group on the ketene-forming transition state. J Org Chem. 2000 Feb 25;65(4):1239-42. doi: 10.1021/jo991473v. PMID: 10814082.
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Asymmetric alpha-alkylation of phenylacetates using 2-alkylamino-2'-hydroxy-1,1'-binaphthyls as chiral auxiliaries.

Enantiomer

Kawamura M, Kurahashi T, Shiraishi S, Kudo K.
PMID: 12643305
Enantiomer. 2002 Nov-Dec;7(6):251-60. doi: 10.1080/10242430215713.

alpha-Alkylation of 2-phenylacetate ester of 2-alkylamino-2'-hydroxy-1,1'-binaphthyls with various alkyl iodides proceeded with good stereoselectivities. An intramolecular hydrogen bonding between N-H group and the carbonyl oxygen seemed to play an important role for asymmetric induction. The auxiliary was also applicable...

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Kawamura M, Kurahashi T, Shiraishi S, et al. Asymmetric alpha-alkylation of phenylacetates using 2-alkylamino-2'-hydroxy-1,1'-binaphthyls as chiral auxiliaries. Enantiomer. 2002;7(6):251-60doi: 10.1080/10242430215713.
Kawamura, M., Kurahashi, T., Shiraishi, S., & Kudo, K. (2002). Asymmetric alpha-alkylation of phenylacetates using 2-alkylamino-2'-hydroxy-1,1'-binaphthyls as chiral auxiliaries. Enantiomer, 7(6), 251-60. https://doi.org/10.1080/10242430215713
Kawamura, Masato, et al. "Asymmetric alpha-alkylation of phenylacetates using 2-alkylamino-2'-hydroxy-1,1'-binaphthyls as chiral auxiliaries." Enantiomer vol. 7,6 (2002): 251-60. doi: https://doi.org/10.1080/10242430215713
Kawamura M, Kurahashi T, Shiraishi S, Kudo K. Asymmetric alpha-alkylation of phenylacetates using 2-alkylamino-2'-hydroxy-1,1'-binaphthyls as chiral auxiliaries. Enantiomer. 2002 Nov-Dec;7(6):251-60. doi: 10.1080/10242430215713. PMID: 12643305.
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Facile synthesis and X-ray structure of alkoxy-functionalized dibenzo[fg,op]naphthacenes.

Organic letters

Cheng XH, Höger S, Fenske D.
PMID: 12868865
Org Lett. 2003 Jul 24;5(15):2587-9. doi: 10.1021/ol034626g.

[structure: see text] 1,3-Bis(2-bromophenyl)-2,5-diphenylbenzenes are readily available by the condensation of phenylacetates with the corresponding pyrylium salts and undergo a palladium-catalyzed dehydrohalogenation to give functionalized dibenzo[fg,op]naphthacenes.

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Cheng XH, Höger S, Fenske D. Facile synthesis and X-ray structure of alkoxy-functionalized dibenzo[fg,op]naphthacenes. Org Lett. 2003;5(15):2587-9doi: 10.1021/ol034626g.
Cheng, X. H., Höger, S., & Fenske, D. (2003). Facile synthesis and X-ray structure of alkoxy-functionalized dibenzo[fg,op]naphthacenes. Organic letters, 5(15), 2587-9. https://doi.org/10.1021/ol034626g
Cheng, Xiao Hong, et al. "Facile synthesis and X-ray structure of alkoxy-functionalized dibenzo[fg,op]naphthacenes." Organic letters vol. 5,15 (2003): 2587-9. doi: https://doi.org/10.1021/ol034626g
Cheng XH, Höger S, Fenske D. Facile synthesis and X-ray structure of alkoxy-functionalized dibenzo[fg,op]naphthacenes. Org Lett. 2003 Jul 24;5(15):2587-9. doi: 10.1021/ol034626g. PMID: 12868865.
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Conformational Analysis and Electronic Interactions of Some 4'-Substituted-2-ethylthio-phenylacetates.

The journal of physical chemistry. A

Rodrigues DN, Ducati LC, Olivato PR, Dal Colle M.
PMID: 25839322
J Phys Chem A. 2015 Apr 23;119(16):3823-32. doi: 10.1021/acs.jpca.5b01531. Epub 2015 Apr 13.

The conformational analysis of various 4'-substituted-2-ethylthio-phenylacetate compounds bearing the substituents NO2 (1), Cl (2), H (3), Me (4), and OMe (5) was performed using infrared (IR) spectroscopic analysis of the carbonyl stretching band (νCO) supported by B3LYP/6-31G(d,p), NBO, QTAIM,...

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Rodrigues DN, Ducati LC, Olivato PR, et al. Conformational Analysis and Electronic Interactions of Some 4'-Substituted-2-ethylthio-phenylacetates. J Phys Chem A. 2015;119(16):3823-32doi: 10.1021/acs.jpca.5b01531.
Rodrigues, D. N., Ducati, L. C., Olivato, P. R., & Dal Colle, M. (2015). Conformational Analysis and Electronic Interactions of Some 4'-Substituted-2-ethylthio-phenylacetates. The journal of physical chemistry. A, 119(16), 3823-32. https://doi.org/10.1021/acs.jpca.5b01531
Rodrigues, Daniel N S, et al. "Conformational Analysis and Electronic Interactions of Some 4'-Substituted-2-ethylthio-phenylacetates." The journal of physical chemistry. A vol. 119,16 (2015): 3823-32. doi: https://doi.org/10.1021/acs.jpca.5b01531
Rodrigues DN, Ducati LC, Olivato PR, Dal Colle M. Conformational Analysis and Electronic Interactions of Some 4'-Substituted-2-ethylthio-phenylacetates. J Phys Chem A. 2015 Apr 23;119(16):3823-32. doi: 10.1021/acs.jpca.5b01531. Epub 2015 Apr 13. PMID: 25839322.
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(R)-Trifluoro- and Difluoropyruvaldehyde N,S-Ketals: Chiral Synthetic Equivalents of beta-Trifluoro and beta-Difluoro alpha-Amino Aldehydes.

The Journal of organic chemistry

Volonterio A, Vergani B, Crucianelli M, Zanda M, Bravo P.
PMID: 11672366
J Org Chem. 1998 Oct 16;63(21):7236-7243. doi: 10.1021/jo980602p.

A new, efficient, and stereoselective two-step approach to stereochemically defined chiral nonracemic gamma-tri- and gamma-difluoro beta-amino alcohols (70% to >95% ee) is described, using tri- and difluoropyruvaldehyde N,S-ketals (R)-1a,b as starting materials. Addition of Grignard reagents to (R)-1 occurs...

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Volonterio A, Vergani B, Crucianelli M, et al. (R)-Trifluoro- and Difluoropyruvaldehyde N,S-Ketals: Chiral Synthetic Equivalents of beta-Trifluoro and beta-Difluoro alpha-Amino Aldehydes. J Org Chem. 1998;63(21):7236-7243doi: 10.1021/jo980602p.
Volonterio, A., Vergani, B., Crucianelli, M., Zanda, M., & Bravo, P. (1998). (R)-Trifluoro- and Difluoropyruvaldehyde N,S-Ketals: Chiral Synthetic Equivalents of beta-Trifluoro and beta-Difluoro alpha-Amino Aldehydes. The Journal of organic chemistry, 63(21), 7236-7243. https://doi.org/10.1021/jo980602p
Volonterio, Alessandro, et al. "(R)-Trifluoro- and Difluoropyruvaldehyde N,S-Ketals: Chiral Synthetic Equivalents of beta-Trifluoro and beta-Difluoro alpha-Amino Aldehydes." The Journal of organic chemistry vol. 63,21 (1998): 7236-7243. doi: https://doi.org/10.1021/jo980602p
Volonterio A, Vergani B, Crucianelli M, Zanda M, Bravo P. (R)-Trifluoro- and Difluoropyruvaldehyde N,S-Ketals: Chiral Synthetic Equivalents of beta-Trifluoro and beta-Difluoro alpha-Amino Aldehydes. J Org Chem. 1998 Oct 16;63(21):7236-7243. doi: 10.1021/jo980602p. PMID: 11672366.
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Ketene-forming eliminations from aryl phenylacetates promoted by R2NH/R2NH2+ in aqueous MeCN. Mechanistic borderline between E2 and E1cb.

The Journal of organic chemistry

Cho BR, Jeong HC, Seung YJ, Pyun SY.
PMID: 12126411
J Org Chem. 2002 Jul 26;67(15):5232-8. doi: 10.1021/jo025555m.

Elimination reactions of 2-X-4-NO2C6H3CH2C(O)OC6H3-2-Y-4-NO2 [X = H (1), NO2 (2)] promoted by R2NH/R2NH2+ in 70 mol % MeCN(aq) have been studied kinetically. The base-promoted eliminations from 1 proceeded by the E2 mechanism when Y = Cl, CF3, and NO2....

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Cho BR, Jeong HC, Seung YJ, et al. Ketene-forming eliminations from aryl phenylacetates promoted by R2NH/R2NH2+ in aqueous MeCN. Mechanistic borderline between E2 and E1cb. J Org Chem. 2002;67(15):5232-8doi: 10.1021/jo025555m.
Cho, B. R., Jeong, H. C., Seung, Y. J., & Pyun, S. Y. (2002). Ketene-forming eliminations from aryl phenylacetates promoted by R2NH/R2NH2+ in aqueous MeCN. Mechanistic borderline between E2 and E1cb. The Journal of organic chemistry, 67(15), 5232-8. https://doi.org/10.1021/jo025555m
Cho, Bong Rae, et al. "Ketene-forming eliminations from aryl phenylacetates promoted by R2NH/R2NH2+ in aqueous MeCN. Mechanistic borderline between E2 and E1cb." The Journal of organic chemistry vol. 67,15 (2002): 5232-8. doi: https://doi.org/10.1021/jo025555m
Cho BR, Jeong HC, Seung YJ, Pyun SY. Ketene-forming eliminations from aryl phenylacetates promoted by R2NH/R2NH2+ in aqueous MeCN. Mechanistic borderline between E2 and E1cb. J Org Chem. 2002 Jul 26;67(15):5232-8. doi: 10.1021/jo025555m. PMID: 12126411.
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Extraction of some metal phenylacetates into chloroform.

Talanta

Adam J, Pribil R, Vselý V.
PMID: 18961125
Talanta. 1972 Jun;19(6):825-7. doi: 10.1016/0039-9140(72)80018-3.

Phenylacetic acid has been found to be very useful as a reagent in the extraction of large quantities of certain ions, notable iron(III), cobalt(II), copper(II), lead, zinc, cadmium and uranyl. A 1M solution of the reagent in chloroform is...

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Adam J, Pribil R, Vselý V. Extraction of some metal phenylacetates into chloroform. Talanta. 1972;19(6):825-7doi: 10.1016/0039-9140(72)80018-3.
Adam, J., Pribil, R., & Vselý, V. (1972). Extraction of some metal phenylacetates into chloroform. Talanta, 19(6), 825-7. https://doi.org/10.1016/0039-9140(72)80018-3
Adam, J, et al. "Extraction of some metal phenylacetates into chloroform." Talanta vol. 19,6 (1972): 825-7. doi: https://doi.org/10.1016/0039-9140(72)80018-3
Adam J, Pribil R, Vselý V. Extraction of some metal phenylacetates into chloroform. Talanta. 1972 Jun;19(6):825-7. doi: 10.1016/0039-9140(72)80018-3. PMID: 18961125.
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New Approach to 4-Phenyl-β-aminotetralin from 4-(3-Halophenyl)tetralen-2-ol Phenylacetate.

Tetrahedron letters

Vincek AS, Booth RG.
PMID: 20161011
Tetrahedron Lett. 2009 Sep 09;50(36):5107-5109. doi: 10.1016/j.tetlet.2009.06.099.

Mixed trifluoroacetyl phenylacetyl anhydride and 3-halostyrenes (fluoro, chloro, and bromo) or vinylcycloalkanes (cyclohexyl, cyclooctyl), undergo cascade Friedel-Crafts cycli-acylalkylation, enolization, and O-acylation to give 4-substituted tetralen-2-ol phenylacetates, without additional solvent in good yields. Base alcoholysis of 4-phenyltetralen-2-ol phenylacetate reveals the...

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Vincek AS, Booth RG. New Approach to 4-Phenyl-β-aminotetralin from 4-(3-Halophenyl)tetralen-2-ol Phenylacetate. Tetrahedron Lett. 2009;50(36):5107-5109doi: 10.1016/j.tetlet.2009.06.099.
Vincek, A. S., & Booth, R. G. (2009). New Approach to 4-Phenyl-β-aminotetralin from 4-(3-Halophenyl)tetralen-2-ol Phenylacetate. Tetrahedron letters, 50(36), 5107-5109. https://doi.org/10.1016/j.tetlet.2009.06.099
Vincek, Adam S, and Booth, Raymond G. "New Approach to 4-Phenyl-β-aminotetralin from 4-(3-Halophenyl)tetralen-2-ol Phenylacetate." Tetrahedron letters vol. 50,36 (2009): 5107-5109. doi: https://doi.org/10.1016/j.tetlet.2009.06.099
Vincek AS, Booth RG. New Approach to 4-Phenyl-β-aminotetralin from 4-(3-Halophenyl)tetralen-2-ol Phenylacetate. Tetrahedron Lett. 2009 Sep 09;50(36):5107-5109. doi: 10.1016/j.tetlet.2009.06.099. PMID: 20161011; PMCID: PMC2758692.
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Supramolecular systems as microreactors: control of product selectivity in organic phototransformation.

Accounts of chemical research

Tung CH, Wu LZ, Zhang LP, Chen B.
PMID: 12534303
Acc Chem Res. 2003 Jan;36(1):39-47. doi: 10.1021/ar010141l.

This Account reviews the developments in microreactor-controlled selectivity in organic phototransformation. Photocycloaddition of alpha,omega-diaryl compounds with long flexible chains within Y-type zeolite and low-density polyethylene films leads to formation of intramolecular cyclomers to the exclusion of intermolecular products. ZSM-5...

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Tung CH, Wu LZ, Zhang LP, et al. Supramolecular systems as microreactors: control of product selectivity in organic phototransformation. Acc Chem Res. 2003;36(1):39-47doi: 10.1021/ar010141l.
Tung, C. H., Wu, L. Z., Zhang, L. P., & Chen, B. (2003). Supramolecular systems as microreactors: control of product selectivity in organic phototransformation. Accounts of chemical research, 36(1), 39-47. https://doi.org/10.1021/ar010141l
Tung, Chen-Ho, et al. "Supramolecular systems as microreactors: control of product selectivity in organic phototransformation." Accounts of chemical research vol. 36,1 (2003): 39-47. doi: https://doi.org/10.1021/ar010141l
Tung CH, Wu LZ, Zhang LP, Chen B. Supramolecular systems as microreactors: control of product selectivity in organic phototransformation. Acc Chem Res. 2003 Jan;36(1):39-47. doi: 10.1021/ar010141l. PMID: 12534303.
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Alkyl alpha (2-dialkylaminoalkoxy) phenylacetates.

Journal of the American Chemical Society

TRUITT P, MARK D.
PMID: 18105973
J Am Chem Soc. 1948 Dec;70(12):4214. doi: 10.1021/ja01192a069.

No abstract available.

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TRUITT P, MARK D. Alkyl alpha-(2-dialkỳlaminoalkoxy)-phenylacetates. Alkyl alpha (2-dialkylaminoalkoxy) phenylacetates. J Am Chem Soc. 1948;70(12):4214doi: 10.1021/ja01192a069.
TRUITT, P., & MARK, D. (1948). Alkyl alpha-(2-dialkỳlaminoalkoxy)-phenylacetates. Alkyl alpha (2-dialkylaminoalkoxy) phenylacetates. Journal of the American Chemical Society, 70(12), 4214. https://doi.org/10.1021/ja01192a069
TRUITT, P, and MARK, D. "Alkyl alpha-(2-dialkỳlaminoalkoxy)-phenylacetates." Alkyl alpha (2-dialkylaminoalkoxy) phenylacetates. Journal of the American Chemical Society vol. 70,12 (1948): 4214. doi: https://doi.org/10.1021/ja01192a069
TRUITT P, MARK D. Alkyl alpha-(2-dialkỳlaminoalkoxy)-phenylacetates. Alkyl alpha (2-dialkylaminoalkoxy) phenylacetates. J Am Chem Soc. 1948 Dec;70(12):4214. doi: 10.1021/ja01192a069. Swedish. PMID: 18105973.
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