126226-17-3Relevant academic research and scientific papers
REGIOSELECTIVE ELECTROPHILIC ADDITIONS TO 2-OXYGENATED-7-OXABICYCLOHEPT-5-ENES: A SIMPLE ENTRY INTO THE 4,7-DIOXATRICYCLO3,6>OCTANE SKELATON
Arjona, Odon,Pradilla, Roberto Fernandez de la,Plumet, Joaquin,Viso, Alma
, p. 4565 - 4578 (1989)
The regio- and stereoselectivity of the reaction between PhSeCl and PhSCl and a number of 7-oxabicyclohept-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-dioxatricyclo3,6>octane derivatives, PhSCl affords a good yield of 5-exo-methyl-2-exo-phenylsulfenyl-4,7-dioxatricyclo>3.2.1.o3,6>octane.
