Efficient Construction of Benzohydrindenones from Aryltrienones via Domino Nazarov Electrocyclization — Electrophilic Aromatic Substitution.

Cindy C. Browder; Fredrik P. Marmsaeter; F. G. West

doi:10.1002/chin.200432116

Efficient Construction of Benzohydrindenones from Aryltrienones via Domino Nazarov Electrocyclization — Electrophilic Aromatic Substitution.

ChemInform ◽

10.1002/chin.200432116 ◽

2004 ◽

Vol 35 (32) ◽

Author(s):

Cindy C. Browder ◽

Fredrik P. Marmsaeter ◽

F. G. West

Keyword(s):

Electrophilic Aromatic Substitution ◽

Aromatic Substitution ◽

Efficient Construction

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Efficient construction of benzohydrindenones from aryltrienones via domino Nazarov electrocyclization electrophilic aromatic substitution

Canadian Journal of Chemistry ◽

10.1139/v03-203 ◽

2004 ◽

Vol 82 (2) ◽

pp. 375-385 ◽

Cited By ~ 21

Author(s):

Cindy C Browder ◽

Fredrik P Marmsäter ◽

F G West

Keyword(s):

Low Temperature ◽

Lewis Acid ◽

Quantitative Yield ◽

Electrophilic Aromatic Substitution ◽

Side Chains ◽

Aromatic Substitution ◽

Nazarov Cyclization ◽

Efficient Construction

1,4-Dien-3-ones substituted with pendant arylethyl side chains attached at C-1 were readily prepared from substituted dihydrocinnamaldehydes. Treatment with TiCl4 at low temperature effected domino Nazarov electrocyclization arene trapping within 5 min to give racemic benzohydrindenones in near-quantitative yield and with complete diastereoselectivity.Key words: domino process, electrophilic aromatic substitution, Lewis acid, Nazarov cyclization.

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An Inquiry-Based Approach to Electrophilic Aromatic Substitution: Quantifying and Identifying Nitration Products by 1H NMR

ACS Symposium Series - NMR Spectroscopy in the Undergraduate Curriculum, Volume 4: In-Person and Distance Learning Approaches ◽

10.1021/bk-2021-1376.ch005 ◽

2021 ◽

pp. 67-78

Author(s):

Nanette M. Wachter ◽

Nicole Wedad Khouryawad ◽

Haley E. Tarbox

Keyword(s):

1H Nmr ◽

Electrophilic Aromatic Substitution ◽

Aromatic Substitution

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Electrophilic Aromatic Substitution

Organic Reaction Mechanisms Series - Organic Reaction Mechanisms 2018 ◽

10.1002/9781119531975.ch5b ◽

2021 ◽

pp. 191-226

Author(s):

G. W. Weaver

Keyword(s):

Electrophilic Aromatic Substitution ◽

Aromatic Substitution

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Reactivity and selectivity of the methoxycarbonyl cation in gas-phase electrophilic aromatic substitution

The Journal of Physical Chemistry ◽

10.1021/j100119a029 ◽

1993 ◽

Vol 97 (17) ◽

pp. 4421-4426 ◽

Cited By ~ 12

Author(s):

Pierluigi Giacomello ◽

Federico Pepi

Keyword(s):

Gas Phase ◽

Electrophilic Aromatic Substitution ◽

Aromatic Substitution

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ChemInform Abstract: ELECTROPHILIC AROMATIC SUBSTITUTION. PART 28. RATE FACTORS FOR PROTIODETRITIATION OF ALL POSITIONS OF HEXAHELICENE (BENZO(C)NAPHTHO(1,2-G)PHENANTHRENE): THE REACTIVITY OF BENT BENZENE RINGS

Chemischer Informationsdienst ◽

10.1002/chin.198126110 ◽

1981 ◽

Vol 12 (26) ◽

Author(s):

W. J. ARCHER ◽

Y. EL-DIN SHAFIG ◽

R. TAYLOR

Keyword(s):

Electrophilic Aromatic Substitution ◽

Aromatic Substitution ◽

Benzene Rings

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ChemInform Abstract: ALUMINA-CATALYZED IPSO ATTACK IN ELECTROPHILIC AROMATIC SUBSTITUTION- METHYLATION OF 2,6-XYLENOL TO 2,3,6-TRIMETHYLPHENOL

Chemischer Informationsdienst ◽

10.1002/chin.197837191 ◽

1978 ◽

Vol 9 (37) ◽

Author(s):

B. E. LEACH

Keyword(s):

Electrophilic Aromatic Substitution ◽

Aromatic Substitution

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ChemInform Abstract: Crystal Structure, Conformational Analyses, and Charge Density Distributions for ent-Epifisetinidol: An Explanation for Regiospecific Electrophilic Aromatic Substitution of 5-Deoxyflavans.

ChemInform ◽

10.1002/chin.199344299 ◽

2010 ◽

Vol 24 (44) ◽

pp. no-no

Author(s):

F. L. TOBIASON ◽

F. R. FRONCZEK ◽

J. P. STEYNBERG ◽

E. C. STEYNBERG ◽

R. W. HEMINGWAY

Keyword(s):

Crystal Structure ◽

Charge Density ◽

Electrophilic Aromatic Substitution ◽

Aromatic Substitution ◽

Density Distributions

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Substituent effects in electrophilic aromatic substitution. A laboratory in organic chemistry

Journal of Chemical Education ◽

10.1021/ed054p450 ◽

1977 ◽

Vol 54 (7) ◽

pp. 450 ◽

Cited By ~ 3

Author(s):

Helmuth Gilow

Keyword(s):

Organic Chemistry ◽

Substituent Effects ◽

Electrophilic Aromatic Substitution ◽

Aromatic Substitution

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Side-chain electrophilic aromatic substitution in 2-alkyloxa- and 2-alkylthiazolines initiated via σ-complex formation with super-electrophilic DNBF: a model proinsecticideElectronic supplementary information (ESI) available: the ABX analysis of the CH2-α and H2 proton region of the adduct 5-Oa. See http://www.rsc.org/suppdata/p2/b2/b201045n/

Journal of the Chemical Society Perkin Transactions 2 ◽

10.1039/b201045n ◽

2002 ◽

pp. 871-877 ◽

Cited By ~ 2

Author(s):

Jean-Claude Cherton ◽

Sandrine Hamm ◽

Marie-José Pouet ◽

Jean-Claude Halle ◽

François Terrier

Keyword(s):

Complex Formation ◽

Supplementary Information ◽

Side Chain ◽

Electrophilic Aromatic Substitution ◽

Aromatic Substitution

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Electrophilic aromatic substitution. Part 27. Chemical selectivities disguised by mass diffusion. Part 6. The kinetics of nitration in aqueous sulphuric acid of durene (1,2,4,5-tetramethylbenzene), nitrodurene, and nitroprehnitene (nitro-1,2,3,4-tetramethylbenzene). A comparison of the rates of nitration of methylnitrobenzenes in aqueous sulphuric acid with the corresponding rates from mixing–disguised nitrations with nitronium hexafluorophosphate in nitromethane based on a theoretical mixing–reaction model

Journal of the Chemical Society Perkin Transactions 2 ◽

10.1039/p29810001358 ◽

1981 ◽

pp. 1358-1366 ◽

Cited By ~ 4

Author(s):

Ajay K. Manglik ◽

Roy B. Moodie ◽

Kenneth Schofield ◽

Erol Dedeoglu ◽

Andreas Dutly ◽

...

Keyword(s):

Sulphuric Acid ◽

Reaction Model ◽

Mass Diffusion ◽

Electrophilic Aromatic Substitution ◽

Aromatic Substitution ◽

Kinetics Of

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Efficient Construction of Benzohydrindenones from Aryltrienones via Domino Nazarov Electrocyclization — Electrophilic Aromatic Substitution.

Efficient construction of benzohydrindenones from aryltrienones via domino Nazarov electrocyclization  electrophilic aromatic substitution

An Inquiry-Based Approach to Electrophilic Aromatic Substitution: Quantifying and Identifying Nitration Products by 1H NMR

Electrophilic Aromatic Substitution

Reactivity and selectivity of the methoxycarbonyl cation in gas-phase electrophilic aromatic substitution

ChemInform Abstract: ELECTROPHILIC AROMATIC SUBSTITUTION. PART 28. RATE FACTORS FOR PROTIODETRITIATION OF ALL POSITIONS OF HEXAHELICENE (BENZO(C)NAPHTHO(1,2-G)PHENANTHRENE): THE REACTIVITY OF BENT BENZENE RINGS

ChemInform Abstract: ALUMINA-CATALYZED IPSO ATTACK IN ELECTROPHILIC AROMATIC SUBSTITUTION- METHYLATION OF 2,6-XYLENOL TO 2,3,6-TRIMETHYLPHENOL

ChemInform Abstract: Crystal Structure, Conformational Analyses, and Charge Density Distributions for ent-Epifisetinidol: An Explanation for Regiospecific Electrophilic Aromatic Substitution of 5-Deoxyflavans.

Substituent effects in electrophilic aromatic substitution. A laboratory in organic chemistry

Efficient construction of benzohydrindenones from aryltrienones via domino Nazarov electrocyclization electrophilic aromatic substitution