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Brandi‐Guarna Reaction
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Abstract
The Brandi‐Guarna reaction is a group of reactions for forming tetrahydropyridone derivatives. It involves the initial 1,3‐dipolar cycloaddition of nitrones and alkylidenecyclopropanes to yield the mixtures of isoxazolidine regioisomers with spiro‐fused cyclopropane rings located on the C‐4 and C‐5, respectively, and the thermolysis of the 1,3‐dipolar cycloadducts via a unique hemolytic cleavage of the weak nitrogen‐oxygen bond accompanying by the subsequent opening of the adjacent cyclopropane ring and closure of the diradical to afford tetrahydropyridones;
N
‐bridgehead bicyclic ketones are ultimately formed from the cyclic nitrones. In addition, the analogous reactions involving the
1,3‐Dipolar
Cycloaddition
of alkylidenecyclopropanes and nitrile oxides followed by similar ring enlargement to form
aza
‐heterocycles are also referred to as the Brandi reaction.
Title: Brandi‐Guarna Reaction
Description:
Abstract
The Brandi‐Guarna reaction is a group of reactions for forming tetrahydropyridone derivatives.
It involves the initial 1,3‐dipolar cycloaddition of nitrones and alkylidenecyclopropanes to yield the mixtures of isoxazolidine regioisomers with spiro‐fused cyclopropane rings located on the C‐4 and C‐5, respectively, and the thermolysis of the 1,3‐dipolar cycloadducts via a unique hemolytic cleavage of the weak nitrogen‐oxygen bond accompanying by the subsequent opening of the adjacent cyclopropane ring and closure of the diradical to afford tetrahydropyridones;
N
‐bridgehead bicyclic ketones are ultimately formed from the cyclic nitrones.
In addition, the analogous reactions involving the
1,3‐Dipolar
Cycloaddition
of alkylidenecyclopropanes and nitrile oxides followed by similar ring enlargement to form
aza
‐heterocycles are also referred to as the Brandi reaction.
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