Reactions of Thiiranium and Sulfonium Ions with Alkenes in the Gas Phase

• Published in: Journal of organic chemistry Vol. 84; no. 16; pp. 10076 - 10087
• Main Authors: Brydon, Samuel C, Lim, Shea Fern, Khairallah, George N, Maître, Philippe, Loire, Estelle, da Silva, Gabriel, O’Hair, Richard A. J, White, Jonathan M
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society 16.08.2019; Amer Chemical Soc
• Subjects: Analytical chemistry; Chemical Sciences; Chemistry; Chemistry, Organic; Organic chemistry; Physical Sciences; Science & Technology; DENSITY FUNCTIONALS; CARBON; SPECTROSCOPY; EPISELENONIUM ION; SELENIRANIUM IONS; REACTIVITY; SULFENOFUNCTIONALIZATION; TRAP; SUBSTITUTION-REACTIONS; PI-LIGAND EXCHANGE

Ion–molecule reactions between thiiranium ion 11 (m/z 213) and cyclohexene and cis-cyclooctene resulted in the formation of addition products 17a and 17b (m/z 295 and m/z 323, respectively) via an electrophilic addition pathway. Associative π-ligand exchange involving direct transfer of the PhS+ moi...