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. Author manuscript; available in PMC: 2008 Sep 6.
Published in final edited form as: J Am Chem Soc. 2006 Mar 1;128(8):2540–2541. doi: 10.1021/ja057163d

Table 1.

Oxidation of Allylic Esters and Carbonatesgraphic file with name nihms-64017-f0003.jpg

Entry Substrate Product Phosphine Yield (time)
1 graphic file with name nihms-64017-t0004.jpg graphic file with name nihms-64017-t0005.jpg PPh3 100% (<1 h)
2 PMePh2 95% (<1 h)
3 dppf 80% (2 h)
4 dppb 73% (26 h)a
5 graphic file with name nihms-64017-t0006.jpg graphic file with name nihms-64017-t0007.jpg PPh3 92% (1 h)
6 graphic file with name nihms-64017-t0008.jpg graphic file with name nihms-64017-t0009.jpg PPh3 96% (>1 h)
7 graphic file with name nihms-64017-t0010.jpg graphic file with name nihms-64017-t0011.jpg PPh3 88% (> 1 h)
8 graphic file with name nihms-64017-t0012.jpg graphic file with name nihms-64017-t0013.jpg PPh3 R=OTBS, 95% (2 h)
9 PPh3 R=OH, 82% (2 h)
10 graphic file with name nihms-64017-t0014.jpg graphic file with name nihms-64017-t0015.jpg PPh3 71% (3 h)b
11 graphic file with name nihms-64017-t0016.jpg graphic file with name nihms-64017-t0017.jpg PPh3 53% (2.5 h)
12 rac-2 97% (4 h)
a

95% brsm.

b

Volatile material. Actual yield may be higher.