Tetrahedron p. 5437 - 5452 (1991)
Update date:2022-07-30
Topics:
Kobayashi, Kazuhiro
Itoh, Masahito
Sasaki, Akiyoshi
Suginome, Hiroshi
New general methods are described for the synthesis of phthalides, 3-monosubstituted, and 3,3-disubstituted phthalides including naturally-occuring phthalides such as pierardine based on a regioselective single or double β-scission of the alkoxyl radicals generated by the photolysis of the hypoiodites of 1-ethyl-benzocyclobuten-1-ols or 1,2-catacondensed benzocyclobuten-1-ols or 1,3-dihydro-1,3-alkanoisobenzofuran-1-ols.The formation paths of the phthalides, which involve a regioselective single or double β-scission of the alkoxyl radicals generated from 1-alkylbenzocyclobuten-1-ols and from catacondensed benzocyclobuten-1-ols, are discussed.Key Words: Synthesis of Phthalides; Alkoxy Radicals; Mercury(II)oxide-Iodine Reagent; Photolysis; Double β-Scission
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