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. 2013 Jul 11;114(1):194–232. doi: 10.1021/cr400107q

Figure 30.

Figure 30

Unimolecular nucleophilic substitution mechanism of retinoid isomerization. The key feature is the generation of a carbocation (retinylic cation) intermediate with lowered bond order that allows rotation around the 11–12 bond to occur. Dissociation of the ester moiety can be facilitated by a Brønsted or Lewis acid catalyst (X).