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   DIMROTH rearrangement

The Dimroth rearrangement is an isomerization of heterocycles that consists in a translocation of endo- or exocyclic heteroatoms through a ring-opening-ring-closure sequence. It can be catalyzed by acids, bases, heat or light.

example 1:


example 2:

 

references:

Eur. J. Org. Chem. 2005, 2914.
Heterocycles 2005, 65, 2683.
J. Chem. Soc., Perkin trans. 1 2002, 1574.
Heterocycles 2002, 57, 631.
Adv. Heterocycl. Chem. 1999, 75, 79. (review)
Heterocycles 1998, 48, 359. (review)
J. Org. Chem. 1998, 63, 3213.
Tetrahedron Lett. 1998, 39, 4695.
Biochemistry 1968, 7, 3453.
Ann. 1909, 364, 183.