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			<gallery>
			File:Bergman cyclization.svg\|Bergman cyclization
			File:Bergman ring.png\|Bergman ring
			File:Bergman cyclization nuclSubst.png\|Bergman cyclization nuclSubst
			File:Bergman cyclization IBM2.png\|Bergman cyclization IBM2
			</gallery>

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'''Bergman cyclization''' is an [[organic chemistry]] reaction that involves the thermal rearrangement of [[enyne]]s to produce highly reactive [[diradical]] species. This reaction is named after the American chemist [[Robert G. Bergman]], who first reported it in 1972. Bergman cyclization is a key step in the synthesis of certain [[natural products]] and has applications in the development of [[anticancer]] drugs, particularly those targeting the [[DNA]] of cancer cells.

The process involves the heating of an enyne to generate a diradical intermediate, which can then undergo various reactions, including [[hydrogen]] abstraction and [[cyclization]], to form a new [[carbon-carbon bond]]. The diradical intermediate is highly reactive and can lead to the formation of a variety of products, depending on the specific substrates and conditions used in the reaction.

Bergman cyclization is particularly important in the synthesis of [[cycloaromatization]] products and has been utilized in the synthesis of complex natural products such as the antitumor antibiotic [[calicheamicin]]. The reaction has also been studied for its potential in the development of new [[chemotherapeutic agents]], as the diradicals generated can interact with DNA, causing strand breaks that lead to cell death.

The mechanism of Bergman cyclization involves the formation of a six-membered ring through a [[pericyclic reaction]]. The reaction is highly dependent on the structure of the enyne, with certain substituents and configurations leading to more favorable cyclization conditions. The reaction can proceed under thermal or photochemical conditions, with the latter sometimes offering more control over the reaction pathway and product distribution.

[[Category:Organic chemistry reactions]]
[[Category:Name reactions]]

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Bergman cyclization - Revision history

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