Skip to main content
. 2016 Aug 3;12:1647–1748. doi: 10.3762/bjoc.12.162

Table 19.

Examples of the Smith rearrangement.

Entry Allylic isomer B Allylic isomer C Comments Ref.

1 Inline graphic
429a
Inline graphic
429b
In CDCl3 within 259 h, approximately 5% of B was transformed into C [427]
2 Inline graphic
430a
Inline graphic
430b
In CHCl3 at room temperature within 150 h, the B:C ratio reached 1.8:1 [439]
3 Inline graphic
431a
Inline graphic
431b
In CDCl3 at 40 °C within 3.5 h, B is transformed into C by 20%. In EtOAc at 40 °C, the yield of C was 25–30% [416]
In CHCl3 after 5 d at room temperature, only partial conversion [431]
4 Inline graphic
432a
Inline graphic
432b
In CDCl3, the B:C ratio reached 1:1.5 [439]