text: In type I rearrangements (Y-A-B-X conversion to X-A-B-Y) the two migrating groups are oriented trans to each other and as a result of the rearrangement they migrate to opposite sides. The first example of a dyotropic rearrangement involving a carbon-carbon bond was reported by Cyril A. Grob and Saul Winstein. They observed the interconversion of 2 bromine atoms in a certain steroid. 
  In a straightforward example the two bromine atoms in 3-tert-butyl-trans-1,2-dibromohexane mutarotate by heating. In the transition state both bromine atoms connect symmetrically to both carbon atoms on opposite sides and the reaction is concerted. Stepwise mechanisms in dyotropic reactions have also been investigated. 
  In organic synthesis an important application is the conversion of 4-substituted-gamma-lactones to butyrolactones. Type I dyotropic rearrangements also occur around carbon-oxygen bonds, such as the thermal equilibration of (RSi)RC-O-SiR to (RSi)RC-O-SiR. The 1,2-Wittig rearrangement can also be considered an example of this reaction type. More dyotropic reactions are found involving N-O bonds and N-N bonds.