The Synthesis of Carbazoles from 3-Vinylindoles with Tetracyanoethylene and Dimethyl Acetylenedicarboxylate

Noland, Wayl­and E.; Kuryla, William C.; Lange, Ronald F. M.

doi:10.1021/ja01531a039

Cited by 66 publications

(12 citation statements)

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“…Diels–Alder reactions of vinyl indoles were first described by Noland and co‐workers in 1959 29a. Such transformations form the basis of a very useful strategy for the dearomatization of indoles to construct carbazole frameworks.…”

Section: Dearomatization By Diels–alder and Related Reactionsmentioning

confidence: 99%

Curing and thermal behavior of diglycidyl ether of bisphenol A in the presence of a mixture of amines

Khurana

Narula

Choudhary

2003

J of Applied Polymer Sci

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ABSTRACT:The curing behavior of diglycidyl ether of bisphenol A (DGEBA) was investigated by differential scanning calorimetry with mixtures of silicon-containing amideamines and diaminodiphenyl sulfone (DDS). Silicon-containing amide-amines were prepared by the reaction of 2.5 mol of 4,4Ј-diaminodiphenyl ether (E), 4,4Ј-diaminodiphenyl methane (M), 3,3Ј-diaminodiphenyl sulfone (mS), 4,4Ј-diaminodiphenyl sulfone (pS), bis(3-aminophenyl) methyl phosphine oxide (B), or tris(3-aminophenyl) phosphine oxide (T) with 1 mol of bis(4-chlorobenzoyl) dimethyl silane. Mixtures of the amide-amines and DDS at ratios of 0:1, 0.25:0.75, 0.5:0.5, 0.75:0.25, and 1:0 were used to investigate the curing behavior of DGEBA. A single exotherm was observed on curing with a mixture of amide-amine and DDS. This clearly shows that the mixture participated in the cocuring reaction. The peak exotherm temperature depended on the structure and the molar ratio of amideamines. With all of the amide-amines and DDS, a significant decrease in the kick-off temperature of the curing exotherm was observed on the incorporation of a 0.25 molar fraction of amide-amines. Thus, with the mixture, the curing temperatures were reduced and were lowest for ether-containing amide-amines and highest for methylene-containing amideamines. The char yield was almost similar in the samples cured with amide-amines (E, pS, or mS) or DDS. The char yield was higher than for either of the constituents when a mixture was used. A synergistic behavior was observed when a mixture of E, M, mS, or pS and DDS was used, whereas mixture of B or T and DDS showed antigonism in the char yield.

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Section: Dearomatization By Diels–alder and Related Reactionsmentioning

confidence: 99%

Curing and thermal behavior of diglycidyl ether of bisphenol A in the presence of a mixture of amines

Khurana

Narula

Choudhary

2003

J of Applied Polymer Sci

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“…A stronger acceptor, TCNE, undergoes a similar reaction without irradiation to give tricyanovinylindole after the elimination of HCN by pyridine (pseudoexcitation band in Scheme 10) [47].…”

Section: Reactions Of Indoles With Unsaturated Acceptorsmentioning

confidence: 99%

A Mechanistic Spectrum of Chemical Reactions

Inagaki

2009

Orbitals in Chemistry

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The mechanism of chemical reactions between electron donors and acceptors continuously changes with the power of the donors and the acceptors. The interaction between the HOMO (d) of the donors and the LUMO (a*) of the acceptors or delocalization of electrons is important for the reactions. The electron d-to-a* transferred configuration mixes to a significant extent. As the donors and/or the acceptors are strong, their excited configurations appreciably mixes together with the transferred configuration. The d-a and d*-a* orbital interactions are important in addition to the d-a* interaction. Reactions have features characteristic of the excited-state reactions although the donor-acceptor system is not really excited, but in the ground state. This process is termed pseudoexcitation. The a-d-a*-d* interaction is important. For much stronger donors and acceptors, the electron transferred configuration is stable and predominant. Covalent bonds do not form but instead ionic pairs, and electron transfer results. A mechanistic spectrum of chemical reactions is composed of the delocalization, pseudoexcitation, and electron transfer bands.

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“…It is well established that photocyclization reactions of 3-cyanovinyl-2-aryl-or 3-cyanovinyl-2-heteroarylindoles can be used to synthesize carbazoles [9][10][11][12]. However, all attempts to react 4 with dimethyl [14].…”

mentioning

confidence: 99%

Synthetic applications of 3-(cyanoacetyl)indoles and related compounds

Slätt¹,

Janosik²,

Wahlström³

et al. 2005

Journal of Heterocyclic Chemistry

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Various synthetic applications of 3-(cyanoacetyl)indoles, as well as syntheses of some related indoles, have been investigated. Diethyl 2-(1H-indol-3-yl)-2-oxoethylphosphonate and a methyl derivative thereof have been prepared in one step from indole. Moreover, it was demonstrated that 3-(cyanoacetyl)indoles are useful starting materials for the preparation of for example 3-(1H-indol-3-yl)-3-oxopropanamides, 3-heteroarylindoles or 3-heteroaroylindoles.

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The Synthesis of Carbazoles from 3-Vinylindoles with Tetracyanoethylene and Dimethyl Acetylenedicarboxylate

Cited by 66 publications

References 2 publications

Curing and thermal behavior of diglycidyl ether of bisphenol A in the presence of a mixture of amines

Curing and thermal behavior of diglycidyl ether of bisphenol A in the presence of a mixture of amines

A Mechanistic Spectrum of Chemical Reactions

Synthetic applications of 3-(cyanoacetyl)indoles and related compounds

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