Diazoalkane 1,3-dipolar cycloaddition

The Diazoalkane 1,3-dipolar cycloaddition is a

dipolarophile. When the dipolarphile is an alkene, the reaction product is a pyrazoline.^[1]

The reaction product of a cycloaddition between

syn addition, and the configuration in the dipolarophile is preserved. The 1-pyrazoline is unstable and isomerizes to the 2-pyrazoline due to favorable conjugation with the ester

group.

With

organic oxidation of the 2-pyrazoline to the pyrazole

.

Another example of a diazo cycloaddition is a

diazo-thioketone coupling

.

References

^ Brückner, Reinhard, Advanced organic chemistry: reaction mechanisms
doi:10.1016/j.tetlet.2004.04.097
.

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[1] Brückner, Reinhard, Advanced organic chemistry: reaction mechanisms

[2] :10.1016/j.tetlet.2004.04.097
.

[1]