1,3-Dipolar cycloaddition

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The 1,3-dipolar cycloaddition, also known as the Huisgen cycloaddition or Huisgen reaction, [1] [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 and others investigated a range of 1,3-dipoles and dipolarophiles. These included:


  1. Huisgen, Rolf (November 1963). "Kinetics and Mechanism of 1,3-Dipolar Cycloadditions". Angewandte Chemie International Edition. 2 (11): 633–645. doi:10.1002/anie.196306331.
  2. Huisgen, Rolf (October 1963). "1,3-Dipolar Cycloadditions. Past and Future". Angewandte Chemie International Edition. 2 (10): 565–598. doi:10.1002/anie.196305651.

ar:إضافة حلقية 3,1-ثنائية القطبية