Formation of radicals by irradiation of alkyl halides in the presence of triethylamine

Cossy, Janine; Ranaivosata, Jean-Luc; Bellosta, Véronique

doi:10.1016/0040-4039(94)88271-1

Cited by 51 publications

(20 citation statements)

References 13 publications

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“…Alkyl bromides and iodides yield C-centered radicals simply on irradiation in the presence of an excess of triethylamine. [102] That this procedure was suitable for ring closures was demonstrated by the isolation of bicyclic ether 53 in almost quantitative yield on subjecting the bromotetrahydropyran derivative 52 to this operation (Scheme 13).…”

Section: Assorted Allies On the March Away From Tinmentioning

confidence: 97%

Flight from the Tyranny of Tin: The Quest for Practical Radical Sources Free from Metal Encumbrances

Baguley¹,

Walton

1998

Angewandte Chemie International Edition

339

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An urgent search is being made for generic reagents that promote free radical synthetic transformations as means of banishing the toxic threat of organotin hydrides. Although second-generation tin reagents are beguiling, organosilanes and a range of thiocarbonyl compounds are more intrinsically benign. Metal-free radical chain sequences based around cyclohexadiene derivatives are being developed (see reaction scheme), and tetrathiafulvalenes mimic metals and allow a crossover from homolytic to ionic chemistry. Z=alkene.

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Section: Assorted Allies On the March Away From Tinmentioning

confidence: 97%

Flight from the Tyranny of Tin: The Quest for Practical Radical Sources Free from Metal Encumbrances

Baguley¹,

Walton

1998

Angewandte Chemie International Edition

339

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“…C-zentrierte Radikale. [102] Daû diese Reaktion für Ringschluûreaktionen geeignet ist, wurde mit der nahezu quantitativen Isolierung des bicyclischen Ethers 53 gezeigt, wobei das Bromtetrahydropyranderivat 52 als Edukt eingesetzt wurde (Schema 13).…”

Section: Verbündete Auf Dem Marsch Fort Vom Zinnunclassified

Flucht vor der Tyrannei des Zinns: auf der Suche nach metallfreien Radikalquellen

Baguley¹,

Walton

1998

Angewandte Chemie

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Dringend gesucht werden neue Reagentien, die Reaktionen freier Radikale vermitteln, um den Problemen ein Ende zu setzen, die mit Organozinnhydriden einhergehen (vor allem deren hohe Toxizität). Zwar wurden schon Fortschritte bei zinnorganischen Reagentien erzielt, z. B. hinsichtlich der Abtrennbarkeit von den Produkten, doch genießen Organosiliciumverbindungen und etliche Thiocarbonylverbindungen ein weitaus besseres Ansehen. Radikalische Reaktionssequenzen ausgehend von Cyclohexadienderivaten als „proaromatischen”︁ Verbindungen wurden entwickelt (siehe Schema), und mit Tetrathiafulvalenen lassen sich Umwandlungen im Grenzgebiet zwischen radikalischen und ionischen Reaktionen durchführen. Z=Alken

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“…In recent reports, donors of hydrogen atoms (organostannane) and potentially hazardous/toxic radical initiators (Et 3 B/O 2 , peroxides, AIBN; see Table for abbreviations used in this Minireview) were utilized for carbon‐centered radical formation from unactivated organohalide . With a great attention on sustainable chemistry, current reports have shown the progress toward the utilize of photoredox catalysis, which offers safe, competent, and waste‐reducing methods to produce organic radicals …”

Section: Introductionmentioning

confidence: 99%

Recent Developments in Radical‐Mediated Transformations of Organohalides

Lekkala

Balakrishna

et al. 2019

Eur J Org Chem

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In recent years, radical‐mediated transformations of organohalides, a class of powerful chemical transformations, have become an important field at the forefront of organic chemistry. Formation of free‐radicals from organohalides is among the most useful methods to access open‐shell reactive intermediates that have a number of established applications in chemical synthesis. Herein we summarize most of the strategies involving metal‐catalyzed, non‐metal‐catalyzed, as well as catalyst‐free radical‐mediated transformations of organohalides.

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Formation of radicals by irradiation of alkyl halides in the presence of triethylamine

Cited by 51 publications

References 13 publications

Flight from the Tyranny of Tin: The Quest for Practical Radical Sources Free from Metal Encumbrances

Flight from the Tyranny of Tin: The Quest for Practical Radical Sources Free from Metal Encumbrances

Flucht vor der Tyrannei des Zinns: auf der Suche nach metallfreien Radikalquellen

Recent Developments in Radical‐Mediated Transformations of Organohalides

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