Table 1 Optimization of reaction conditions

From: Electrochemical Ferrier rearrangement of glycals in flow

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Entry

Variations from the standard conditions

Yield (%)b

1a

none

94 (86)c

2

0.1 M, 2.5 mA·cm−2, 0.1 F·mol−1

85

3

1.0 mA·cm−2, 0.025 F·mol−1

72

4

4.0 mA·cm−2, 0.1 F·mol−1

93

5

tR = 1 min, 4.0 mA·cm−2

94

6

tR = 18 s, 13.3 mA·cm−2

91

7

nBu4NBF4 as electrolyte

26

8

nBu4NPF6 as electrolyte

89

9

under argon

94

10

dry CH3CN

92

11

graphite anode

traces

12

stainless steel cathode

20

13

no electricity

0

  1. a Reaction conditions: tri-O-acetyl-D-glucal 1a (1.0 equiv.), benzyl alcohol 2b (2.0 equiv.), nBu4NClO4 (0.1 equiv.), CH3CN (0.2 M), impervious graphite anode/graphite cathode, 2.0 mA·cm−2, 0.05 F·mol−1, room temperature, 0.15 mL·min−1 flow rate, 2 min residence time. b Yields were determined by 1H NMR analysis of the crude mixture, using diglyme as an internal standard. c Isolated yield.