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. Author manuscript; available in PMC: 2012 Sep 28.
Published in final edited form as: J Am Chem Soc. 2011 Sep 2;133(38):14940–14943. doi: 10.1021/ja206743v

Table 1.

Lewis acid-promoted C3-nucleophile substitution.

graphic file with name nihms323492t1.jpg
Entry Nucleophile Solvent, Temp (°C) graphic file with name nihms323492t2.jpg Yield (%)a
1 graphic file with name nihms323492t3.jpg CH2Cl2, 23 graphic file with name nihms323492t4.jpg 77 (6.3:1)b
2 graphic file with name nihms323492t5.jpg EtNO2, −45c graphic file with name nihms323492t6.jpg 50 (17:1)b
3 graphic file with name nihms323492t7.jpg CH2Cl2, 23 graphic file with name nihms323492t8.jpg 60
4 graphic file with name nihms323492t9.jpg CH2Cl2, 23 graphic file with name nihms323492t10.jpg 52
5 graphic file with name nihms323492t11.jpg CH2Cl2, 23 graphic file with name nihms323492t12.jpg 91
6 graphic file with name nihms323492t13.jpg CH2Cl2, 23 graphic file with name nihms323492t14.jpg 89
7 graphic file with name nihms323492t15.jpg CH2Cl2, 23 graphic file with name nihms323492t16.jpg 50
8 graphic file with name nihms323492t17.jpg EtNO2, −45c graphic file with name nihms323492t18.jpg 26 (3.9:1)d
9 graphic file with name nihms323492t19.jpg EtNO2, −45c graphic file with name nihms323492t20.jpg 54 (2.4:1)d
10 graphic file with name nihms323492t21.jpg EtNO2, 23c graphic file with name nihms323492t22.jpg 59
a

Isolated yield; average of two experiments; AgSbF6 (2.0 equiv) and nucleophile (2.0 equiv).

b

Regioisomeric ratios determined by 1H NMR. Major regioisomer shown.

c

18-crown-6 (2.0 equiv).

d

The minor regioisomer is the para-adduct.