Supplementary Materials

Teaching an old carbocation new tricks: Intermolecular C—H insertion reactions of vinyl cations

Stasik Popov, Brian Shao, Alex L. Bagdasarian, Tyler R. Benton, Luyi Zou, Zhongyue Yang, K. N. Houk, Hosea M. Nelson

Materials/Methods, Supplementary Text, Tables, Figures, and/or References

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  • Materials and Methods
  • Supplementary Text
  • Figs. S1 to S44
  • Tables S1 and S2
  • Captions for Movies S1 to S5
  • References

Images, Video, and Other Media

Movie S1
4,4-dimethylcyclohexene vinyl cation C2 addition. MD Simulation of 4,4-dimethylcyclohexene vinyl cation reacting with cyclohexane. This video follows the reaction progress from a 1,1 insertion to the C2 alkylated product. The second half of the video visualizes the reaction while highlighting the key points throughout. Time scale of 300 fs is illustrated in the video. See supporting computational details for methods, video was animated using CYLView.
Movie S2
4,4-dimethylcyclohexene vinyl cation C1 addition. MD Simulation of 4,4- dimethylcyclohexene vinyl cation reacting with cyclohexane. This video follows the reaction progress from a 1,1 insertion to the C1 alkylated product followed by the 1,2-hydride shift. This was the most common pathway for this substrate. The second half of the video visualizes the reaction while highlighting the key points throughout. Time scale of 300 fs is illustrated in the video. See supporting computational details for methods, video was animated using CYLView.
Movie S3
5,5-dimethylcyclohexene vinyl cation C2 addition. MD Simulation of 5,5-dimethylcyclohexene vinyl cation reacting with cyclohexane. This video follows the reaction progress from a 1,1 insertion to the C2 alkylated product. Time scale of 300 fs is illustrated in the video. See supporting computational details for methods, video was animated using CYLView.
Movie S4
5,5-dimethylcyclohexene vinyl cation C1 addition. MD Simulation of 5,5-dimethylcyclohexene vinyl cation reacting with cyclohexane. This video follows the reaction progress from a 1,1 insertion to the C1 alkylated product followed by the 1,2-hydride shift. This was the most common pathway for this substrate. Time scale of 300 fs is illustrated in the video. See supporting computational details for methods, video was animated using CYLView.
Movie S5
Butenyl vinyl cation reaction with cyclohexane. MD Simulation of but-1-en-2-yl vinyl cation reacting with cyclohexane. This video follows the reaction progress from a 1,1 insertion to the bridging nonclassical carbocation. This was the most common pathway for this
substrate. Time scale of 500 fs is illustrated in the video. See supporting computational details
for methods, video was animated using CYLView.