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- Q809549 subject Q7400638.
- Q809549 subject Q7458901.
- Q809549 abstract "The Barton reaction, also known as the Barton Nitrite Ester Reaction, is a photochemical reaction that involves the photolysis of an alkyl nitrite to form a δ-nitroso alcohol.Discovered in 1960, the reaction is named for its discoverer, Nobel Laureate Sir Derek Barton. Barton’s Nobel Prize in Chemistry in 1969 was awarded for his work on understanding conformations of organic molecules, work which was key to realizing the utility of the Barton Reaction.The Barton Reaction involves a homolytic RO–NO cleavage, followed by δ-hydrogen abstraction, free radical recombination, and tautomerization to form an oxime. Selectivity for the δ-hydrogen is a result of the conformation of the 6-membered radical intermediate. Often, the site of hydrogen atom abstraction can be easily predicted. This allows the regio- and stereo-selective introduction of functionality into complicated molecules with high yield. Due to its then unique ability to derivitize otherwise inert substrates Barton used this reaction extensively in the 1960s to create a number of unnatural steroid analogues.While the Barton reaction has not enjoyed the popularity or widespread use of many other organic reactions, together with the mechanistically similar Hofmann–Löffler reaction it represents one of the first examples of C-H activation chemistry, a field which is now the topic of much frontline research in industrial and academic chemistry circles.".
- Q809549 thumbnail Barton_reaction_mechanism.svg?width=300.
- Q809549 wikiPageWikiLink Q102419.
- Q809549 wikiPageWikiLink Q135171.
- Q809549 wikiPageWikiLink Q1386472.
- Q809549 wikiPageWikiLink Q156.
- Q809549 wikiPageWikiLink Q16814.
- Q809549 wikiPageWikiLink Q182738.
- Q809549 wikiPageWikiLink Q184564.
- Q809549 wikiPageWikiLink Q185056.
- Q809549 wikiPageWikiLink Q213788.
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- Q809549 wikiPageWikiLink Q276843.
- Q809549 wikiPageWikiLink Q334640.
- Q809549 wikiPageWikiLink Q410255.
- Q809549 wikiPageWikiLink Q412815.
- Q809549 wikiPageWikiLink Q414939.
- Q809549 wikiPageWikiLink Q419266.
- Q809549 wikiPageWikiLink Q419812.
- Q809549 wikiPageWikiLink Q422852.
- Q809549 wikiPageWikiLink Q44585.
- Q809549 wikiPageWikiLink Q5876831.
- Q809549 wikiPageWikiLink Q5954884.
- Q809549 wikiPageWikiLink Q629.
- Q809549 wikiPageWikiLink Q7400638.
- Q809549 wikiPageWikiLink Q7458901.
- Q809549 wikiPageWikiLink Q898902.
- Q809549 wikiPageWikiLink Q900254.
- Q809549 wikiPageWikiLink Q908109.
- Q809549 comment "The Barton reaction, also known as the Barton Nitrite Ester Reaction, is a photochemical reaction that involves the photolysis of an alkyl nitrite to form a δ-nitroso alcohol.Discovered in 1960, the reaction is named for its discoverer, Nobel Laureate Sir Derek Barton.".
- Q809549 label "Barton reaction".
- Q809549 depiction Barton_reaction_mechanism.svg.