Tetrahedron p. 4565 - 4578 (1989)
Update date:2022-09-26
Topics:
Arjona, Odon
Pradilla, Roberto Fernandez de la
Plumet, Joaquin
Viso, Alma
The regio- and stereoselectivity of the reaction between PhSeCl and PhSCl and a number of 7-oxabicyclo<2.2.1>hept-5-enes bearing an oxygenated substituent on C-2 is discussed.In most cases, both electrophiles react with complete regio- and stereoselectivity to provide 5-endo-chloro-6-exo-benzeneselenenyl (benzenesulfenyl) derivatives. 7-Oxanorbornen-2-endo-ols behave differently with both electrophiles.Thus, while PhSeCl produces 5-endo-chloro-6-exo-benzeneselenenyl adducts and small amounts of 4,7-dioxatricyclo<3.2.1.03,6>octane derivatives, PhSCl affords a good yield of 5-exo-methyl-2-exo-phenylsulfenyl-4,7-dioxatricyclo>3.2.1.o3,6>octane.
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Doi:10.1016/S0040-4039(00)99334-1
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