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. Author manuscript; available in PMC: 2009 Aug 20.
Published in final edited form as: J Am Chem Soc. 2007 Jul 27;129(33):10282–10294. doi: 10.1021/ja072969u

Table 5.

Desulfurative Rearrangement of Allylic Disulfides in the Absence of Phosphine

graphic file with name nihms62608t107.jpg
Entry Thiol Product Method
PPh3 % yield, E/Z Piperidine % yield, E/Z Heat % yield E/Z
1 graphic file with name nihms62608t108.jpg graphic file with name nihms62608t109.jpg 45

E only		 62

2.6:1		 78

E only
105
2 graphic file with name nihms62608t110.jpg graphic file with name nihms62608t111.jpg - - 67

E only
83 106
3 graphic file with name nihms62608t112.jpg graphic file with name nihms62608t113.jpg - - 68

E only
107
4 Me(CH2)7SH graphic file with name nihms62608t114.jpg - - 75

E only
108
5 4-Me-C6H4-SH graphic file with name nihms62608t115.jpg 18

E only		 66

2.5:1		 66

E only
109
6 PhSH graphic file with name nihms62608t116.jpg - - 63

E only
110
7 4-Cl-C6H4-SH graphic file with name nihms62608t117.jpg - - 62

E only
111
8 4-NO2-C6H4SH graphic file with name nihms62608t118.jpg - - 20

E only
112
9 2-PySH graphic file with name nihms62608t119.jpg - - 45

E only
113
10 2-HO-C6H4SH graphic file with name nihms62608t120.jpg - - 57

E only
114