Journal of Organic Chemistry p. 1279 - 1282 (1994)
Update date:2022-08-16
Topics:
Mitani, Michiharu
Kiriyama, Takuya
Kuratate, Tomoaki
Polychloro compounds were added to olefins in the presence of semiconductor particles (TiO2 or CdS) under photoirradiation.The photoreaction without semiconductors afforded no adducts at all; however, loading of TiO2 with Ag, Cu, or Fe3O4 enhanced the yield of the photoaddition reaction even further.Semiconductors operate as catalysts for the one-electron injection into the polychloro compounds.The relative adsorptions of the polychloro compounds onto the semiconductor particles correlate with the yields of the adducts, while the half-wave reduction potentials of the polychlorides do not.This semiconductor-catalyzed reaction was selective to unfunctionalized olefins and to those bearing a functional group at a remote position.An alkyne furnished the product via further reduction following addition, i.e., 1,1,3-trichloro-1-heptene (7) from 1-hexyne and carbon tetrachloride.
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