1,3-dipolar cycloaddition
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The 1,3-dipolar cycloaddition, also known as the Huisgen cycloaddition or Huisgen reaction, [#endnote_1] [#endnote_2] is an organic chemical reaction belonging to the larger class of cycloadditions. It is the reaction between a 1,3-dipole and a dipolarophile, most of which are substituted alkenes, to form a five-membered ring. Rolf Huisgen first saw the prospects of varying the 1,3-dipole and its high value for synthesis of 5-membered heterocycles.
Classes of 1,3-dipoles
Huisgen investigated a range of 1,3-dipoles and dipolarophiles. These included:- Azides and alkynes react in the Azide alkyne Huisgen cycloaddition.
- Diazo compounds are 1,3-dipoles in the Diazoalkane 1,3-dipolar cycloaddition.
- Ozonolysis begins with a 1,3-dipolar cycloaddition of ozone. This is followed by a retro-1,3-dipolar cycloaddition and then a 1,3-dipolar cycloaddition of the fragments.
References
- ↑ Kinetics and Mechanism of 1,3-Dipolar Cycloadditions R. Huisgen Angewandte Chemie International Edition Volume 2, Issue 11, Date: November 1963, Pages: 633-645 [Abstract]
- ↑ 1,3-Dipolar Cycloadditions. Past and Future Rolf Huisgen Angewandte Chemie International Edition Volume 2, Issue 10, Date: October 1963, Pages: 565-598 [Abstract]
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