114744-44-4

Upstream product

• 114744-41-1 (1S,2R,4S)-2-Methyl-7-oxa-bicyclo[2.2.1]hept-5-en-2-ol 
• 931-59-9 benzenesulfenyl chloride 
• 917-54-4 methyllithium 
• 95530-78-2 7-oxabicyclo[2.2.1]hept-5-en-2-one 
• 114744-41-1 2-exo-methyl-7-oxabicyclo<2.2.1>hept-5-en-2-endo-ol 

Relevant 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

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.

REGIO- AND STEREOSELECTIVE ELECTROPHILIC ADDITIONS TO EXO AND ENDO-2-HYDROXY-2-METHYL-7-OXABICYCLOHEPT-5-ENE

The regio- and stereoselectivity of electrophilic additions of PhSeCl and PhSCl to isomeric 2-hydroxy-2-methyl-7-oxabicyclohept-5-enes is highly dependent upon the relative stereochemistry of the substrate.