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. 2015 Apr 13;6(6):3329–3333. doi: 10.1039/c5sc00921a

Table 1. Probing the importance of boron positioning and substitution on oxime condensations.

Inline graphic
Entry Ar X Product Conc (µM) Conv b (%)
1 c Ph H graphic file with name c5sc00921a-u2.jpg 100 <5
2 graphic file with name c5sc00921a-u3.jpg H graphic file with name c5sc00921a-u4.jpg 100 >98
3 graphic file with name c5sc00921a-u5.jpg H graphic file with name c5sc00921a-u6.jpg 10 >98
4 graphic file with name c5sc00921a-u7.jpg H graphic file with name c5sc00921a-u8.jpg 100 >98
5 c graphic file with name c5sc00921a-u9.jpg H graphic file with name c5sc00921a-u10.jpg 100 <5
6 c graphic file with name c5sc00921a-u11.jpg H graphic file with name c5sc00921a-u12.jpg 100 <5
7 graphic file with name c5sc00921a-u13.jpg Me graphic file with name c5sc00921a-u14.jpg 100 94
8 graphic file with name c5sc00921a-u15.jpg H graphic file with name c5sc00921a-u16.jpg 100 >98 d
9 graphic file with name c5sc00921a-u17.jpg Me graphic file with name c5sc00921a-u18.jpg 100 >98

aTime is approximate since samples are injected directly after mixing.

bDetermined by reverse phase HPLC analysis under neutral conditions.

cInjections at 90 minutes still show <5% conversion.

dAt the first injection approximately 10% of the pinacol ester oxime is observed, but only the hydrolysed product is detected at 90 minutes. KPi = potassium phosphate buffer.