200617-53-4Relevant academic research and scientific papers
Mechanism of the second sulfenylation of indole
Hamel, Pierre
, p. 2854 - 2858 (2002)
Sulfenylation of indole using a sulfenyl chloride occurs initially at the 3-position of the ring, leading to a 3-indolyl sulfide. When an excess of sulfenyl chloride is used, a second sulfide group is introduced at the 2-position, and an indolyl 2,3-bis-sulfide results. We have demonstrated that this second sulfenylation occurs not by direct introduction of the second sulfide at the 2-position but via initial formation of an indolenium 3,3-bis-sulfide intermediate, followed by migration of one of the sulfide groups to the 2-position. This was achieved by the isolation of two examples of 3H-indole 3,3-bis-sulfides and by subsequent demonstration that they rearrange to the indolyl 2,3-bis-sulfides by treatment with sulfenyl halides.
Isolation of 3H-indole-3,3 bis-sulfides as intermediates in the second sulfenylation of indole
Hamel, Pierre
, p. 8473 - 8474 (1997)
3H-indole-3,3 bis sulfides have been isolated as probable intermediates in the second sulfenylation of indole with sulfenyl halides.
