Carbon dioxide: a reagent for simultaneous protection of nucleophilic centers and the activation of alternative locations to electrophilic attack. V. Activation of the 2-alkyl group of a 2-alkylindole toward proton loss and subsequent electrophilic substitution

Alan R. Katritzky; Kunihiko. Akutagawa

doi:10.1021/ja00281a061

Carbon dioxide: a reagent for simultaneous protection of nucleophilic centers and the activation of alternative locations to electrophilic attack. V. Activation of the 2-alkyl group of a 2-alkylindole toward proton loss and subsequent electrophilic substitution

Journal of the American Chemical Society ◽

10.1021/ja00281a061 ◽

1986 ◽

Vol 108 (21) ◽

pp. 6808-6809 ◽

Cited By ~ 43

Author(s):

Alan R. Katritzky ◽

Kunihiko. Akutagawa

Keyword(s):

Carbon Dioxide ◽

Alkyl Group ◽

Electrophilic Substitution ◽

Electrophilic Attack ◽

Proton Loss

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ChemInform Abstract: Carbon Dioxide: A Reagent for Simultaneous Protection of Nucleophilic Centers and the Activation of Alternative Locations to Electrophilic Attack. Part 5. Activation of the 2-Alkyl Group of a 2-Alkylindole Toward Proton Loss and Subse

ChemInform ◽

10.1002/chin.198710214 ◽

1987 ◽

Vol 18 (10) ◽

Author(s):

A. R. KATRITZKY ◽

K. AKUTAGAWA

Keyword(s):

Carbon Dioxide ◽

Alkyl Group ◽

Electrophilic Attack ◽

Proton Loss

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ChemInform Abstract: Carbon Dioxide: A Reagent for Simultaneous Protection of Nucleophilic Centers and the Activation of Alternative Locations to Electrophilic Attack. Part 10. α-Metalation of Tetrahydroquinoline and Indoline via Their Lithium Carbamates:

ChemInform ◽

10.1002/chin.198918217 ◽

1989 ◽

Vol 20 (18) ◽

Author(s):

A. R. KATRITZKY ◽

S. SENGUPTA

Keyword(s):

Carbon Dioxide ◽

Electrophilic Attack

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ChemInform Abstract: Carbon Dioxide: A Reagent for the Protection of Nucleophilic Centres and the Simultaneous Activation of Electrophilic Attack.

Chemischer Informationsdienst ◽

10.1002/chin.198637211 ◽

1986 ◽

Vol 17 (37) ◽

Author(s):

A. R. KATRITZKY ◽

K. AKUTAGAWA

Keyword(s):

Carbon Dioxide ◽

Electrophilic Attack ◽

Simultaneous Activation

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Supercritical carbon dioxide. 5. Carboxyinversion reactions of diacyl peroxides. Alkyl group rearrangement and carbon dioxide exchange

The Journal of Organic Chemistry ◽

10.1021/jo00385a020 ◽

1987 ◽

Vol 52 (9) ◽

pp. 1754-1757 ◽

Cited By ~ 6

Author(s):

Michael E. Sigman ◽

John T. Barbas ◽

John E. Leffler

Keyword(s):

Carbon Dioxide ◽

Supercritical Carbon Dioxide ◽

Alkyl Group ◽

Carbon Dioxide Exchange ◽

Supercritical Carbon

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ChemInform Abstract: Reactivity of Phosphacarbamates: Transfer of the Carbamate Group Promoted by Metal Assisted Electrophilic Attack at the Carbon Dioxide Moiety.

ChemInform ◽

10.1002/chin.198905218 ◽

1989 ◽

Vol 20 (5) ◽

Author(s):

M. ARESTA ◽

E. QUARANTA

Keyword(s):

Carbon Dioxide ◽

Electrophilic Attack ◽

Carbamate Group

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Carbon dioxide: a reagent for the simultaneous protection of nucleophilic centers and the activation of alternative locations to electrophilic attack. 17. Substitution of N-methyl-1- and N-methyl-2-naphthylamine and side-chain functionalization of o-toluidine

The Journal of Organic Chemistry ◽

10.1021/jo00017a012 ◽

1991 ◽

Vol 56 (17) ◽

pp. 5045-5048 ◽

Cited By ~ 20

Author(s):

Alan R. Katritzky ◽

Michael Black ◽

Wei Qiang Fan

Keyword(s):

Carbon Dioxide ◽

Side Chain ◽

Electrophilic Attack

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Carbon Dioxide: A Peagent for the Protection of Nucleophilic Centres and the Simultaneous Activation to Electrophilic Attack-Part Xii. One-Pot Conversion of 3-Methylindole into 2-Formyl-3-Methylindole

Synthetic Communications ◽

10.1080/00397918808060902 ◽

1988 ◽

Vol 18 (10) ◽

pp. 1151-1158 ◽

Cited By ~ 16

Author(s):

Alan R. Katritzky ◽

Kunihiko Akutagawa ◽

R. Alan Jones

Keyword(s):

Carbon Dioxide ◽

Electrophilic Attack ◽

One Pot ◽

Simultaneous Activation

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Reactivity of phosphacarbamates: transfer of the carbamate group promoted by metal-assisted electrophilic attack at the carbon dioxide moiety

The Journal of Organic Chemistry ◽

10.1021/jo00252a066 ◽

1988 ◽

Vol 53 (17) ◽

pp. 4153-4154 ◽

Cited By ~ 27

Author(s):

Michele Aresta ◽

Eugenio Quaranta

Keyword(s):

Carbon Dioxide ◽

Electrophilic Attack ◽

Carbamate Group

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Carbon dioxide: a reagent for the simultaneous protection of nucleophilic centres and the activation of alternative locations to electrophilic attack

Tetrahedron ◽

10.1016/s0040-4020(01)86820-4 ◽

1987 ◽

Vol 43 (10) ◽

pp. 2343-2348 ◽

Cited By ~ 14

Author(s):

Alan R. Katritzky ◽

Wei-Qiang Fan ◽

Anna E. Koziol ◽

Gus J. Palenik

Keyword(s):

Carbon Dioxide ◽

Electrophilic Attack

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A Comparative Study of the Kinetics of Electrophilic Substitution in Aromatic Substrates by Iodine Monochloride and Iodine in Potassium Iodide

Zeitschrift für Naturforschung A ◽

10.1515/zna-1980-0215 ◽

1980 ◽

Vol 35 (2) ◽

pp. 254-255

Author(s):

T. S. Rao ◽

R. N. Jukar

Keyword(s):

Comparative Study ◽

Potassium Iodide ◽

Electrophilic Substitution ◽

Iodine Monochloride ◽

Electrophilic Attack ◽

Aromatic Substrates ◽

Kinetics Of

Abstract Electrophilic substitution in aromatic substrates by iodine monochloride is about 105 times faster than by iodine in potassium iodide. This is due to the permanent dipole in the iodine monochloride, with iodine as the positive end, which greatly facilitates electrophilic attack.

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