The stereochemistry of the reaction of 2-norbornylmagnesium bromide with formaldehyde Academic Article uri icon

abstract

  • Diastereomeric endo-2-norbornylmagnesium bromide and mixtures of endo- and exo-2-norbornylmagnesium bromide react stereospecifically with retention of configuration at the carbon-magnesium bond with formaldehyde to form the expected primary alcohol. This stereochemical result, which is comparable to that observed previously in electrophilic substitutions of stereoisomeric organomagnesium reagents, is observed even when 5 mole % ferric chloride is added. The stereospecificity observed both with and without added metal salts suggests that single electron transfer is not important in 1,2 addition of sec-alkylmagnesium reagents to simple aliphatic aldehydes. © 1977.

author list (cited authors)

  • Bergbreiter, D. E., & Reichert, O. M.

citation count

  • 8

publication date

  • January 1977