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Qu'est-ce (qui) est nucleal reaction - définition
![Heathcock]]'s synthesis of dihydroprotodaphniphylline features a highly efficient cascade involving two aldehyde/amine condensations, a Prins-like cyclization, and a 1,5-hydride transfer to afford a pentacyclic structure from an acyclic starting material.](https://commons.wikimedia.org/wiki/Special:FilePath/Dihydroprotodaphniphylline synthesis.png?width=200 "Heathcock]]'s synthesis of dihydroprotodaphniphylline features a highly efficient cascade involving two aldehyde/amine condensations, a Prins-like cyclization, and a 1,5-hydride transfer to afford a pentacyclic structure from an acyclic starting material.")
!['''Scheme 11.''' Pericyclic sequence for the synthesis of [2,2]paracyclophanes](https://commons.wikimedia.org/wiki/Special:FilePath/Scheme 11 - peri - pcyclophane.svg?width=200 "'''Scheme 11.''' Pericyclic sequence for the synthesis of [2,2]paracyclophanes")
!['''Scheme 14.''' Gold-catalyzed
formal intramolecular [4+2] cycloaddition of 1,6-enynes](https://commons.wikimedia.org/wiki/Special:FilePath/Scheme 14 - metal - gold enyne.svg?width=200 "'''Scheme 14.''' Gold-catalyzed
formal intramolecular [4+2] cycloaddition of 1,6-enynes")
!['''Scheme 15.''' Proposed cascade process in the formal intramolecular [4+2] cycloaddition of 1,6-enynes](https://commons.wikimedia.org/wiki/Special:FilePath/Scheme 15 - metal - gold enyne mech.svg?width=200 "'''Scheme 15.''' Proposed cascade process in the formal intramolecular [4+2] cycloaddition of 1,6-enynes")
Wikipédia
The Wulff–Dötz reaction (also known as the Dötz reaction or the benzannulation reaction of the Fischer carbene complexes) is the chemical reaction of an aromatic or vinylic alkoxy pentacarbonyl chromium carbene complex with an alkyne and carbon monoxide to give a Cr(CO)3-coordinated substituted phenol. Several reviews have been published. It is named after the German chemist Karl Heinz Dötz (b. 1943) and the American chemist William D. Wulff (b. 1949) at Michigan State University. The reaction was first discovered by Karl Dötz and was extensively developed by his group and W. Wulff's group. They subsequently share the name of the reaction.
The position of the substituents is highly predictable with the largest alkyne substituent (RL) neighboring the phenol and the smallest alkyne substituent (RS) neighboring the methoxy group. Hence, this reaction is more useful for terminal alkynes than internal alkynes.
The phenol can be liberated from the chromium complex by a mild oxidation, such as ceric ammonium nitrate or air oxidation.
Since this reaction can quickly generate complex phenolic compounds, the Wulff–Dötz reaction has been used most often in the synthesis of natural products, especially Vitamins E and K. It is also applicable to the synthesis of polyphenolic compounds, such as calixarenes.
