2024-03-28T17:04:42Z
https://soar-ir.repo.nii.ac.jp/oai
oai:soar-ir.repo.nii.ac.jp:00011892
2022-12-14T04:00:54Z
1169:1170
Synthesis and Reactivity of 3-Methylsulfinyl-2H-cyclohepta[b]furan-2-ones
Higashi, J
Okada, K
Shoji, T
Toyota, K
Watanabe, M
Yasunami, M
Kikuchi, S
Ito, S
Morita, N
2H-Cyclohepta[b]furan-2-one
Dimethyl Sulfide Ditriflate
Trifluoromethanesulfonic Anhydride
Electrophilic Substitution
Coupling
2H-Cyclohepta[b]furan-2-ones (2a,b) reacted with dimethyl sulfide dittiflate to give dimethy](2-oxo-2H-cyclohepta[b]furan-3-yl)sulfonium trifluoromethanesulfonates (3a,b), which were treated with Et3N to give 3-methylthio-2H-cyclohepta[b]furan-2-ones (4a,b). Sulfides 4a and 4b were oxidized with m-CPBA to give corresponding sulfoxides (5a,b) and sulfones (6a,b). The sulfoxides (5a,b) thermally underwent coupling reaction to give 3,3'-bi-2H-cyclohepta[b] furan-2-ones (7a,b). The sulfoxides (5a,b) reacted with trifluoromethanesulfonic anhydride (Tf2O) to afford sulfonium ions 8a and 8b at lower temperature, which reacted with 2a or 2b to give sulfonium ions (9a-c). Treatment of compounds 9a-c with Et2NH or Et3N gave corresponding sulfide products (10a-c).
Article
Heterocycles. Vol 76, Issue 1, 2008, pp.759-770.
journal article
The Japan Institute of Heterocyclic Chemistry
2008
application/pdf
Heterocycles
1
76
759
770
0385-5414
AA00663739
https://soar-ir.repo.nii.ac.jp/record/11892/files/Heterocycles 2008, 76, 759.pdf
eng
http://www.heterocycles.jp/
http://www.heterocycles.jp/
10.3987/COM-08-S(N)85
https://doi.org/10.3987/COM-08-S(N)85
Copyright© 2008 The Japan Institute of Heterocyclic Chemistry