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. 2014 Jul 25;16(16):4154–4157. doi: 10.1021/ol501852n

Table 4. Role of Water in Vinyl Triflate Formation.

graphic file with name ol-2014-01852n_0008.jpg

entry H2O (equiv) R Z/Ea time (h) conva (%)
1 – H – 0.25 39
2 – Me 3.0 3.0 36
3 0.25 H – 0.25 81
4 0.25 Me 1.6 3.0 91
5 0.50 H – 0.25 79
6 0.50 Me 1.2 3.0 90
7 0.75 H – 0.25 75
8 0.75 Me 1.1 3.0 91
9 1.0 H – 0.25 83
10 1.0 Me 1.3 3.0 83
11 1.5 H – 0.25 87
12 1.5 Me 1.0 3.0 73
a

Determined by 1H NMR.