Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 135, Issue 43, Pages 16070-16073Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ja4092648
Keywords
-
Categories
Funding
- Ministry of Education, Culture, Sports, Science & Technology, Japan [2105]
- Grants-in-Aid for Scientific Research [21106001, 25410200, 21106002, 25410115] Funding Source: KAKEN
Ask authors/readers for more resources
Halogen and chalcogen cations (X+ = Br+, I+, ArS+, and ArSe+) were generated by low-temperature electrochemical oxidation in the presence of dimethyl sulfoxide (DMSO) and were accumulated in the solution. DFT calculations indicated that DMSO stabilizes these cations by coordination. The complexes of I+ with one and two DMSO molecules were observed by cold-spray-ionization MS analyses. The stability of the resulting cation pools of X+ increased in the order of Br+ < I+ < ArS+ < ArSe+, which could be explained in terms of the electronegativity of X. The cation pools served as versatile reagents for organic synthesis; the reactions with alkenes gave beta-X-substituted alkoxysulfonium ions, which were converted to the corresponding carbonyl compounds by the treatment with triethylamine, whereas the treatment with methanol gave the corresponding alcohols. The reactions with aminoalkenes and 1,6-dienes gave the cyclized products.
Authors
I am an author on this paper
Click your name to claim this paper and add it to your profile.
Reviews
Recommended
No Data Available