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. 2020 Dec 31;86(2):1685–1700. doi: 10.1021/acs.joc.0c02512

Table 2. Study on the Substituent Effect in the Reaction of Compounds 1 Carried out with 6 equiv of t-BuOK.

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entrya 1–3 R1 R2 R3 R4 R5 2:3 ratiob yield (%)
1 a Me C(O)Me H Cl Cl 0.09:1.00 84c (2a+3a)
2 b Me C(O)Me Me Cl Cl 1.00:0.88d 54c (2b+3b)
3 c Et C(O)Me H Cl Cl 0.13:1.00 90c (2c+3c)
4 d Bn C(O)Me H Cl Cl 0.25:1.00 62c (2d+3d)
5 f Me C(O)Pr H Cl Cl 0.18:1.00 86c (2f+3f)
6 i Me Me H Cl Cl 1:0 85c (2i)
7 l Me C(O)Me H OMe Cl 1:0 74e (2l)
8 n Me C(O)Me H H OMe 1:0 35e (2n)
9 o Me C(O)Me H H H 1:0 59e (2o)
a

Reagents and reaction conditions: substrate (0.6 mmol), t-BuOK (3.6 mmol), THF (3 mL), 30 min, then quenching with H2O.

b

The product ratio of the isolated mixtures was determined by 1H NMR.

c

The reaction was carried out at 25 °C.

d

dr = 1.00:0.16.

e

The reaction was carried out at reflux temperature.