Journal of Organic Chemistry p. 1397 - 1400 (1987)
Update date:2022-08-04
Topics:
Hori, Mikio
Kataoka, Tadashi
Shimizu, Hiroshi
Tsutsumi, Kazuhiro
The thermal reaction of 2-methyl-4-oxo-2-selenoniochroman-3-ide (4) in aprotic solvents afforded (E)-bis<2-<(methylseleno)methyl>benzoyl>ethylene (5) and trans-1,2,3-tris<2-<(methylseleno)methyl>benzoyl>cyclopropane (6) via a carbene intermediate.Ethanol reacted thermally with 4 to open the chroman ring, giving ethyl 2-<(methylseleno)methyl>benzoate (9a) and ethyl 2-(ethoxymethyl)benzoate (10a), whereas reaction with methanol yielded only methyl 2-<(methylseleno)methyl>benzoate (9b).Hydrolysis of ylide 4 eliminated dimethyl selenide, giving phthalide and 2-(hydroxymethyl)benzoic acid.
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