Enediyne- and Tributyltin Hydride-Mediated Aryl Radical Additions onto Various Radical Acceptors

Grissom, Janet Wisniewski; Klingberg, Detlef; Meyenburg, Sabine; Stallman, B. L.

doi:10.1021/jo00104a053

Cited by 46 publications

(22 citation statements)

References 0 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The structural viability of enediyne compounds allows us to incorporate these crosslinking moieties via a relative mild ''post-polymerization modification'' strategy. 43 Another enediyne containing alkyloxyamine compound (7) was synthesized from 8 44 through Mitsunobu reaction and subsequent hydrazinolysis (Scheme 2) in good yield. Reaction of alkyloxyamine with ketones (aldehydes) is known as one type of ''click'' chemistry due to its high efficiency.…”

Section: Resultsmentioning

confidence: 99%

Formation of polymeric nanoparticles via Bergman cyclization mediated intramolecular chain collapse

Zhu

et al. 2011

J. Mater. Chem.

View full text Add to dashboard Cite

Section: Resultsmentioning

confidence: 99%

Formation of polymeric nanoparticles via Bergman cyclization mediated intramolecular chain collapse

Zhu

et al. 2011

J. Mater. Chem.

View full text Add to dashboard Cite

“…Their salts might thus provide new superconductive materials and/or other polymeric systems with novel properties. [66,67] It is important to mention that the parent hydrocarbons 1a, [35][36][37][38] 2a, [39,40] 3a [41] and 4a [42,43] have already been synthetized in laboratories.…”

Section: Discussionmentioning

confidence: 99%

“…It will turn out that the latter exerts a dramatic change in acidity leading to some extremal values in the gas phase and in DMSO. It is gratifying and very important to stress that the chemistry of the cyano group is well known, [32][33][34] and that the parent cyclopentadiene-annulated polycyclic aromatic hydrocarbons 1a, [35][36][37][38] 2a, [39,40] 3a [41] and 4a [42,43] have already been prepared and are known in the literature. Scheme 1.…”

Section: Introductionmentioning

confidence: 99%

Strong Acidity of Some Polycyclic Aromatic Compounds Annulated to a Cyclopentadiene Moiety and Their Cyano Derivatives – A Density Functional B3LYP Study

Vianello

Maksić

2005

Eur J Org Chem

View full text Add to dashboard Cite

The acidity of the parent 1H‐benz[f]indene (1a), 1H‐benz[e]indene (2a), 1H‐benz[fg]acenaphthylene (3a) and 1H‐cyclopenta[l]phenanthrene (4a) and of their polycyano derivatives is examined in the gas phase and in DMSO by the DFT‐B3LYP methods. It is shown that the parent hydrocarbons exhibit modest acidities, whereas a dramatic increase in acidity is observed upon multiple cyanation leading to hyperstrong neutral organic superacids. It is found that polycyano derivatives undergo prototropic tautomerism with a consequence that the most stable tautomer contains a ketene imine C=C=NH functionality. The origin of their highly pronounced acidity is identified as a very strong anionic resonance effect efficiently assisted by a large number of CN groups in a concerted manner. It is stressed that the polycyanated anions are very stable and have a highly dispersed negative charge, which should lead to a low nucleophilicity and weak coordinating properties, thus making them potentially very useful in academic research and technological applications. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)

show abstract

“…In recent years, the enediyne antitumor antibiotics 1 have been widely investigated due to their unique mechanism of DNA-cleavage and their unusual structures. Moreover, the emergence of these naturally occurring, biologically active compounds has sparked extensive investigations in the chemistry of conjugated enediynes, − enyne allenes ,, and enyne ketenes. , While considerable effort has been devoted to the DNA-cleaving ability of the biradical intermediates that arise from these compound families by a cycloaromatization reaction, − less attention has been focused on utilizing these highly reactive intermediates in subsequent radical cyclizations. 1ab,, …”

Section: Introductionmentioning

confidence: 99%

Tandem Enyne Allene−Radical Cyclization: Low-Temperature Approaches to Benz[e]indene and Indene Compounds

et al. 1997

Self Cite

View full text Add to dashboard Cite

In an effort to lower the temperatures required to prepare multicyclic compounds using the tandem enediyne-radical cyclization, we have developed the tandem enyne allene-radical cyclization which proceeds at temperatures as low as 37 degrees C. The reactions were carried out using three different methods for the preparation of the enyne allenes. The first method involved the [3,3] sigmatropic rearrangement of an enediyne followed by a tandem enyne allene-radical cyclization. This reaction could be effected either by thermolysis (150 degrees C) or by AgBF(4) rearrangement followed by heating at 75 degrees C. A second technique utilized a [2,3] sigmatropic shift of an enediyne at -78 degrees C followed by tandem cyclization at 37 or 75 degrees C depending on the substrate. The final method involved the base-catalyzed isomerization of propargyl sulfones which yielded enyne allenes that underwent cyclization at 37 degrees C. These three sequences provide a method for the synthesis of ring systems using conditions that may be compatible with the sensitive functionality needed during the synthesis of complex natural products.

show abstract

Enediyne- and Tributyltin Hydride-Mediated Aryl Radical Additions onto Various Radical Acceptors

Cited by 46 publications

References 0 publications

Formation of polymeric nanoparticles via Bergman cyclization mediated intramolecular chain collapse

Formation of polymeric nanoparticles via Bergman cyclization mediated intramolecular chain collapse

Strong Acidity of Some Polycyclic Aromatic Compounds Annulated to a Cyclopentadiene Moiety and Their Cyano Derivatives – A Density Functional B3LYP Study

Tandem Enyne Allene−Radical Cyclization: Low-Temperature Approaches to Benz[e]indene and Indene Compounds

Contact Info

Product

Resources

About