Skip to main content
. 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 3.

Preparation of Allylic Thiols and the Corresponding Allyl Heteroaryl Disulfides

Allylic Xanthates (% yield) Rearranged Thiocarbamate (% yield) Thiol (% yield) Disulfide (% yield)
graphic file with name nihms62608t55.jpg graphic file with name nihms62608t56.jpg graphic file with name nihms62608t57.jpg graphic file with name nihms62608t58.jpg
61 (80) 62 (99) 63 (93) R = 2-Py 64 (96)
R = 4-NO2-2-Py 65 (86)
R = Bt 66 (81)
graphic file with name nihms62608t59.jpg graphic file with name nihms62608t60.jpg graphic file with name nihms62608t61.jpg graphic file with name nihms62608t62.jpg
67 (92) 68 (99) 69 (−) 70 (15)
graphic file with name nihms62608t63.jpg graphic file with name nihms62608t64.jpg graphic file with name nihms62608t65.jpg graphic file with name nihms62608t66.jpg
71 (80) 72 (83) 73 (87) R = SBt 74 (83)
R = SePh 75 (56)
graphic file with name nihms62608t67.jpg graphic file with name nihms62608t68.jpg graphic file with name nihms62608t69.jpg graphic file with name nihms62608t70.jpg
76 (87) 77 (94) 78 (−) 79 (45 from 77)